Substituted oxadiazoles for combating phytopathogenic fungi

ABSTRACT

The present invention relates the use of the compounds of the formula I 
                         
or the N-oxides, or the agriculturally acceptable salts thereof for combating phytopathogenic harmful fungi, wherein the variables are defined as given in the description and claims. Further present invention relates to novel compounds, to mixtures comprising at least one such compound of the formula I and at least one further pesticidally active substance selected from the group consisting of herbicides, safeners, fungicides, insecticides, and plant growth regulators; and to agrochemical compositions comprising at least one such compound of the formula I and to agrochemical compositions further comprising seeds.

This application is a National Stage application of InternationalApplication No. PCT/EP2016/077819, filed Nov. 16, 2016. This applicationalso claims priority under 35 U.S.C. § 119 to European PatentApplication No. 15195439.3, filed Nov. 19, 2015.

The present invention relates to the use oxadiazoles of the formula I,or an N-oxide and/or their agriculturally useful for controllingphytopathogenic fungi, or to a method for combating phytopathogenicharmful fungi, which process comprises treating the fungi or thematerials, plants, the soil or seeds to be protected against fungalattack, with an effective amount of at least one compound of the formulaI, or an N-oxide, or an agriculturally acceptable salt thereof; thepresent invention also relates to mixtures comprising at least one suchcompound of the formula I and at least one further pesticidally activesubstance selected from the group consisting of herbicides, safeners,fungicides, insecticides, and plant growth regulators; and toagrochemical compositions comprising at least one such compound of theformula I and to agrochemical compositions further comprising seeds.

EP 276432 A2 relates to 3-phenyl-5-trifluoromethyloxadiazole derivativesand to their use to combat phytopathogenic microorganisms. WO2013/008162 describes trifluoromethyl-oxadiazole derivatives with HDAC4inhibitory activity and their medical use, particularly in the treatmentof Huntington's disease, muscle atrophy and diabetes/metabolic syndrome.WO11088192, WO 2011088181 describes the medicinal use oftrifluoromethyl-oxadiazole derivatives. A use for controllingphytopathogenic fungi is not described. WO 2015/185485 was publishedafter the date of filing of the present application and describes theuse of certain substituted oxadiazoles for combating phytopathogenicfungi

In many cases, in particular at low application rates, the fungicidalactivity of known fungicidal compounds is unsatisfactory. Based on this,it was an objective of the present invention to provide compounds havingimproved activity and/or a broader activity spectrum againstphytopathogenic fungi. This objective is achieved by the oxadiazoles ofthe formula I and/or their agriculturally useful salts for controllingphytopathogenic fungi.

Accordingly, the present invention relates to the use of the compoundsof the formula I

wherein:

-   A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the    ring member atoms of the heterocyclic ring include besides carbon    atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring    member atoms; and wherein the cyclic groups A are unsubstituted or    substituted by 1, 2, 3 or 4 identical or different groups R^(A);    wherein    -   R^(A) is halogen, cyano, NO₂, OH, NH₂, SH, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,        C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy; and wherein any of the        aliphatic or cyclic moieties are unsubstituted or substituted by        1, 2, 3 or 4 identical or different groups R^(a); wherein        -   R^(a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₁-C₆-alkylthio, C₁-C₆-haloalkylthio or C₃-C₈-cycloalkyl;-   R¹, R² independently of each other are hydrogen, C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,    C(═O)—(C₁-C₆-alkyl), C(═O)—(C₁-C₆-alkoxy), phenyl-C₁-C₄-alkyl,    heteroaryl-C₁-C₄-alkyl, phenyl, naphthyl or a 3- to 10-membered    saturated, partially unsaturated or aromatic mono- or bicyclic    heterocycle, wherein the ring member atoms of said mono- or bicyclic    heterocycle include besides carbon atoms further 1, 2, 3 or 4    heteroatoms selected from N, O and S as ring member atoms and    wherein 1 or 2 carbon ring member atoms of the heterocycle may be    replaced by 1 or 2 groups independently selected from C(═O) and    C(═S); and wherein the heteroaryl group in heteroaryl-C₁-C₄-alkyl is    a 5- or 6-membered aromatic heterocycle, wherein the ring member    atoms of the heterocyclic ring include besides carbon atoms 1, 2, 3    or 4 heteroatoms selected from N, O and S as ring member atoms; and    wherein any of the above-mentioned aliphatic or cyclic groups are    unsubstituted or substituted by 1, 2, 3 or up to the maximum    possible number of identical or different groups R^(1a); or-   R¹ and R² together with the nitrogen atom to which they are bound    form a saturated or partially unsaturated mono- or bicyclic 3- to    7-membered heterocycle, wherein the heterocycle includes beside one    nitrogen atom and one or more carbon atoms no further heteroatom or    1, 2 or 3 further heteroatoms independently selected from N, O and S    as ring member atoms; and wherein one or two CH₂ groups of the    heterocycle may be replaced by one or two groups independently    selected from the group of C(═O) and C(═S); and wherein the    heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the    maximum possible number of identical or different groups R^(1a);    wherein    -   R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,        NHSO₂—C₁-C₄-alkyl, (C═O)—(C₁-C₄-alkyl), C(═O)—(C₁-C₄-alkoxy) or        C₁-C₆-alkylsulfonyl;-   R³ is H, C₁-C₄-alkyl, C₁-C₄-haloalkyl;-   R⁴ is H, C₁-C₄-alkyl, C₁-C₄-haloalkyl;-   or the N-oxides, or the agriculturally acceptable salts thereof for    combating phytopathogenic harmful fungi.

Agriculturally acceptable salts of the compounds of the formula Iencompass especially the salts of those cations or the acid additionsalts of those acids whose cations and anions, respectively, have noadverse effect on the fungicidal action of the compounds I. Suitablecations are thus in particular the ions of the alkali metals, preferablysodium and potassium, of the alkaline earth metals, preferably calcium,magnesium and barium, of the transition metals, preferably manganese,copper, zinc and iron, and also the ammonium ion which, if desired, maycarry one to four C₁-C₄-alkyl substituents and/or one phenyl or benzylsubstituent, preferably diisopropylammonium, tetramethylammonium,tetrabutylammonium, trimethylbenzylammonium, furthermore phosphoniumions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, andsulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium. Anions ofacceptable acid addition salts are primarily chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting a compound I with an acid ofthe corresponding anion, preferably of hydrochloric acid, hydrobromicacid, sulfuric acid, phosphoric acid or nitric acid.

Compounds of the formula I can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersarising from restricted rotation about a single bond of asymmetricgroups and geometric isomers. They also form part of the subject matterof the present invention. One skilled in the art will appreciate thatone stereoisomer may be more active and/or may exhibit beneficialeffects when enriched relative to the other stereoisomer(s) or whenseparated from the other stereoisomer(s). Additionally, the skilledartisan knows how to separate, enrich, and/or to selectively preparesaid stereoisomers. The compounds of the invention may be present as amixture of stereoisomers, e.g. a racemate, individual stereoisomers, oras an optically active form.

Compounds of the formula I can be present in different crystalmodifications whose biological activity may differ. They also form partof the subject matter of the present invention. In respect of thevariables, the embodiments of the intermediates obtained duringpreparation of compounds I correspond to the embodiments of thecompounds of formula I. The term “compounds I” refers to compounds offormula I.

In the definitions of the variables given above, collective terms areused which are generally representative for the substituents inquestion. The term “C_(n)-C_(m)” indicates the number of carbon atomspossible in each case in the substituent or substituent moiety inquestion.

The moieties having two ore more possibilities to be attached applyfollowing:

The moieties having no brackets in the name are bonded via the lastmoiety e.g. C₂-C₆-alkenyloxyimino-C₁-C₄-alkyl is bonded via C₁-C₄-alkyl,heteroaryl-C₁-C₄-alkyl is bonded via C₁-C₄-alkyl etc.

The moieties having brackets in the name are bonded via the first moietye.g. C(═O)—(C₁-C₆-alkyl) is bonded via C═O as indicated by the numbervalence of the carbon atom, etc.

The term “halogen” refers to fluorine, chlorine, bromine and iodine.

The term “C₁-C₆-alkyl” refers to a straight-chained or branchedsaturated hydrocarbon group having 1 to 6 carbon atoms, for examplemethyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl, and 1,1-dimethylethyl.

The term “C₁-C₆-haloalkyl” refers to a straight-chained or branchedalkyl group having 1 to 6 carbon atoms (as defined above), wherein someor all of the hydrogen atoms in these groups may be replaced by halogenatoms as mentioned above, for example chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl,2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH₂—C₂F₅,CF₂—C₂F₅, CF(CF₃)₂, 1-(fluoromethyl)-2-fluoroethyl,1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.

The term “C₁-C₆-alkoxy” refers to a straight-chain or branched alkylgroup having 1 to 6 carbon atoms (as defined above) which is bonded viaan oxygen, at any position in the alkyl group, for example methoxy,ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,2-methylpropoxy or 1,1-dimethylethoxy.

The term “C₁-C₆-haloalkoxy” refers to a C₁-C₆-alkoxy group as definedabove, wherein some or all of the hydrogen atoms may be replaced byhalogen atoms as mentioned above, for example, OCH₂F, OCHF₂, OCF₃,OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC₂F₅,2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅,1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy,1-(CH₂Br)-2-bromo¬ethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxyor nonafluorobutoxy. The terms “phenyl-C₁-C₄-alkyl orheteroaryl-C₁-C₄-alkyl” refer to alkyl having 1 to 4 carbon atoms (asdefined above), wherein one hydrogen atom of the alkyl radical isreplaced by a phenyl or hetereoaryl radical respectively.

The term “C₁-C₄-alkoxy-C₁-C₄-alkyl” refers to alkyl having 1 to 4 carbonatoms (as defined above), wherein one hydrogen atom of the alkyl radicalis replaced by a C₁-C₄-alkoxy group (as defined above). Likewise, theterm “C₁-C₄-alkylthio-C₁-C₄-alkyl” refers to alkyl having 1 to 4 carbonatoms (as defined above), wherein one hydrogen atom of the alkyl radicalis replaced by a C₁-C₄-alkylthio group.

The term “C₁-C₆-alkylthio” as used herein refers to straight-chain orbranched alkyl groups having 1 to 6 carbon atoms (as defined above)bonded via a sulfur atom. Accordingly, the term “C₁-C₆-haloalkylthio” asused herein refers to straight-chain or branched haloalkyl group having1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, atany position in the haloalkyl group.

The term “C₁-C₆-alkylsulfinyl” refers to straight-chain or branchedalkyl groups having 1 to 6 carbon atoms (as defined above) bondedthrough a —S(═O)— moiety, at any position in the alkyl group, forexample methylsulfinyl and ethylsulfinyl, and the like. Accordingly, theterm “C₁-C₆-haloalkylsulfinyl” refers to straight-chain or branchedhaloalkyl group having 1 to 6 carbon atoms (as defined above), bondedthrough a —S(═O)— moiety, at any position in the haloalkyl group.

The term “C₁-C₆-alkylsulfonyl” refers to straight-chain or branchedalkyl groups having 1 to 6 carbon atoms (as defined above), bondedthrough a —S(═O)₂— moiety, at any position in the alkyl group, forexample methylsulfonyl. Accordingly, the term “C₁-C₆-haloalkylsulfonyl”refers to straight-chain or branched haloalkyl group having 1 to 6carbon atoms (as defined above), bonded through a —S(═O)₂— moiety, atany position in the haloalkyl group.

The term “hydroxyC₁-C₄-alkyl” refers to alkyl having 1 to 4 carbonatoms, wherein one hydrogen atom of the alkyl radical is replaced by aOH group.

The term “aminoC₁-C₄-alkyl” refers to alkyl having 1 to 4 carbon atoms,wherein one hydrogen atom of the alkyl radical is replaced by a NH₂group.

The term “C₁-C₄-alkylamino-C₁-C₄-alkyl” refers to refers to alkyl having1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of thealkyl radical is replaced by a C₁-C₄-alkyl-NH— group which is boundthrough the nitrogen. Likewise the term “diC₁-C₄-alkylamino-C₁-C₄-alkyl”refers to refers to alkyl having 1 to 4 carbon atoms (as defined above),wherein one hydrogen atom of the alkyl radical is replaced by a(C₁-C₄-alkyl)₂N— group which is bound through the nitrogen.

The term “aminocarbonyl-C₁-C₄-alkyl” refers to alkyl having 1 to 4carbon atoms, wherein one hydrogen atom of the alkyl radical is replacedby a —(C═O)—NH₂ group.

The term “C₂-C₆-alkenyl” refers to a straight-chain or branchedunsaturated hydrocarbon radical having 2 to 6 carbon atoms and a doublebond in any position, such as ethenyl, 1-propenyl, 2-propenyl (allyl),1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.

The term “C₂-C₆-alkynyl” refers to a straight-chain or branchedunsaturated hydrocarbon radical having 2 to 6 carbon atoms andcontaining at least one triple bond, such as ethynyl, 1-propynyl,2-propynyl (propargyl), 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl.

The term “C₃-C₈-cycloalkyl” refers to monocyclic saturated hydrocarbonradicals having 3 to 8 carbon ring members such as cyclopropyl (C₃H₅),cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

The term “C₃-C₈-cycloalkyloxy” refers to a cycloalkyl radical having 3to 8 carbon atoms (as defined above), which is bonded via an oxygen.

The term “C(═O)—(C₁-C₄-alkyl)” refers to a radical which is attachedthrough the carbon atom of the C(═O) group as indicated by the numbervalence of the carbon atom.

The term “aliphatic” refers to compounds or radicals composed of carbonand hydrogen and which are non-aromatic compounds. An alicyclic compoundor radical is an organic compound that is both aliphatic and cyclic.They contain one or more all-carbon rings which may be either saturatedor unsaturated, but do not have aromatic character.

The terms “cyclic moiety” or “cyclic group” refer to a radical which isan alicyclic ring or an aromatic ring, such as, for example, phenyl orheteroaryl.

The term “and wherein any of the aliphatic or cyclic groups areunsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possiblenumber of identical or different groups Ria” refers to aliphatic groups,cyclic groups and groups, which contain an aliphatic and a cyclic moietyin one group, such as in, for example, phenyl-C₁-C₄-alkyl; therefore agroup which contains an aliphatic and a cyclic moiety both of thesemoieties may be substituted or unsubstituted independently of eachother.

The term “heteroaryl” refers to aromatic monocyclic or polycyclic ringsystems incuding besides carbon atoms, 1, 2, 3 or 4 heteroatomsindependently selected from the group consisting of N, O and S.

The term “phenyl” refers to an aromatic ring systems incuding six carbonatoms (commonly referred to as benzene ring). In association with thegroup A the term “phenyl” is to be interpreted as a benzene ring orphenylene ring, which is attached to both, the oxadiazole moiety and the—CR³R⁴— group.

The term “saturated or partially unsaturated 3-, 4-, 5-, 6- or7-membered carbocycle” is to be understood as meaning both saturated orpartially unsaturated carbocycles having 3, 4, 5, 6 or 7 ring members.Examples include cyclopropyl, cyclopentyl, cyclopentenyl,cyclopentadienyl, cyclohexyl, cyclohexenyl, cyclohexadienyl,cycloheptyl, cycloheptenyl, cycloheptadienyl, and the like.

The term “3- to 10-membered saturated, partially unsaturated or aromaticmono- or bicyclic heterocycle, wherein the ring member atoms of saidmono- or bicyclic heterocycle include besides carbon atoms further 1, 2,3 or 4 heteroatoms selected from N, O and S as ring member atoms”, is tobe understood as meaning both, aromatic mono- and bicyclicheteroaromatic ring systems, and also saturated and partiallyunsaturated heterocycles, for example:

a 3- or 4-membered saturated heterocycle which contains 1 or 2heteroatoms from the group consisting of N, O and S as ring members suchas oxirane, aziridine, thiirane, oxetane, azetidine, thiethane,[1,2]dioxetane, [1,2]dithietane, [1,2]diazetidine; and a 5- or6-membered saturated or partially unsaturated heterocycle which contains1, 2 or 3 heteroatoms from the group consisting of N, O and S as ringmembers such as 2-tetrahydro-furanyl, 3-tetrahydrofuranyl,2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl,3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl,3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl,3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl,3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl,4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl,4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl,4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl,4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl,4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl,4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl,2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl,3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl,1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl and also thecorresponding -ylidene radicals; and

a 7-membered saturated or partially unsaturated heterocycle such astetra- and hexahydroazepinyl, such as2,3,4,5-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or -7-yl,3,4,5,6-tetrahydro[2H]azepin-2-,-3-,-4-,-5-,-6- or -7-yl,2,3,4,7-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6-or -7-yl,2,3,6,7-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or -7-yl,hexahydroazepin-1-,-2-,-3- or -4-yl, tetra- and hexahydrooxepinyl suchas 2,3,4,5-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or -7-yl,2,3,4,7-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or -7-yl,2,3,6,7-tetrahydro[1H]oxepin-2-, -3-,-4-,-5-,-6- or -7-yl,hexahydroazepin-1-,-2-,-3- or -4-yl, tetra- andhexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra-and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl,tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyland the corresponding -ylidene radicals; and

the term “5- or 6-membered heteroaryl” or the term “5- or 6-memberedaromatic heterocycle” refers to aromatic ring systems incuding besidescarbon atoms, 1, 2, 3 or 4 heteroatoms independently selected from thegroup consisting of N, O and S, for example, a 5-membered heteroarylsuch as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl,furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl,pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl,isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl,1,2,4-triazol-3-yl1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl;or

a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl,pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

In respect of the variables, the embodiments of the intermediatescorrespond to the embodiments of the compounds I. Preference is given tothose compounds I and, where applicable, also to compounds of allsub-formulae provided herein, wherein all variables have independentlyof each other or more preferably in combination (any possiblecombination of 2 or more substituents as defined herein) the followingmeanings:

In one aspect of the invention A is phenyl which is unsubstituted orsubstituted by 1, 2, 3 or 4 identical or different groups R^(A) asdefined or preferably defined herein and wherein the group—C(R³R⁴)—NR¹R² is attached to the phenyl ring in para-position withregard to the trifluoromethyloxadiazole group.

In one aspect of the invention A is phenyl which is unsubstituted orsubstituted by 1, 2, 3 or 4 identical or different groups R^(A) asdefined or preferably defined herein and wherein the group—C(R³R⁴)—NR¹R² is attached to the phenyl ring in meta-position withregard to the trifluoromethyloxadiazole group.

In a further aspect of the invention A is phenyl which is substituted by1 or 2 identical or different groups R^(A) as defined or preferablydefined herein and wherein the group —C(R³R⁴)—NR¹R² is attached to thephenyl ring in pars-position with regard to thetrifluoromethyloxadiazole group.

In another aspect of the invention A is phenyl which is unsubstitutedand wherein the group —C(R³R⁴)—NR¹R² is attached to the phenyl ring inpars-position with regard to the trifluoromethyloxadiazole group.

In a preferred embodiment of the invention A is phenyl substituted byR^(A) selected from halogen, or C₁-C₆-alkyl. In a further preferredembodiment of the invention A is phenyl substituted by halogen. In aspecial preferred embodiment of the invention A is phenyl substituted byF. In a further special preferred embodiment of the invention A isphenyl substituted by Cl.

In a further preferred embodiment of the invention A is phenylsubstituted by C₁-C₆-alkyl. In a special preferred embodiment of theinvention A is phenyl substituted by CH₃. In a further special preferredembodiment of the invention A is phenyl substituted by CH₂CH₃. In afurther special preferred embodiment of the invention A is phenyl whichis unsubstituted.

In one embodiment A is a 6-membered aromatic heterocycle, wherein thering member atoms of the aromatic heterocycle include besides carbonatoms 1 or 2 nitrogen atoms as ring member atoms; and wherein thearomatic heterocyclic ring is unsubstituted or substituted by 1 or 2identical or different groups R^(A) as defined or preferably definedherein.

In a further embodiment A is a 6-membered aromatic heterocycle, whereinthe ring member atoms of the aromatic heterocycle include besides carbonatoms 1 or 2 nitrogen atoms as ring member atoms; and wherein thearomatic heterocycle is unsubstituted or substituted by 1 or 2 identicalor different groups R^(A) as defined or preferably defined herein andwherein the group —C(R³R⁴)—NR¹R² is attached to the 6-membered aromaticheterocycle in pars-position with regard to thetrifluoromethyloxadiazole group.

In a further embodiment A is a 6-membered aromatic heterocycle, whereinthe ring member atoms of the aromatic heterocycle include besides carbonatoms 1 or 2 nitrogen atoms as ring member atoms; and wherein thearomatic heterocycle is unsubstituted or substituted by 1 or 2 identicalor different groups R^(A) as defined or preferably defined herein andwherein the group —C(R³R⁴)—NR¹R² is attached to the 6-membered aromaticheterocycle in meta-position with regard to thetrifluoromethyloxadiazole group.

In a further embodiment A is a 6-membered aromatic heterocycle, whereinthe ring member atoms of the aromatic heterocycle include besides carbonatoms 1 or 2 nitrogen atoms as ring member atoms; and wherein thearomatic heterocycle is unsubstituted or substituted by 1 or 2 identicalor different groups R^(A) as defined or preferably defined herein andwherein the group —C(R³R⁴)—NR¹R² is attached to the 6-membered aromaticheterocycle in ortho-position with regard to thetrifluoromethyloxadiazole group.

In a further embodiment A is a 6-membered aromatic heterocycle, whereinthe ring member atoms of the aromatic heterocycle include besides carbonatoms 1 or 2 nitrogen atoms as ring member atoms; and wherein thearomatic heterocycle is unsubstituted and wherein the group—C(R³R⁴)—NR¹R² is attached to the 6-membered aromatic heterocycle inpars-position with regard to the trifluoromethyloxadiazole group.

In a further preferred embodiment A is a 5-membered aromaticheterocycle, wherein the ring member atoms of the heterocycle includebesides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and Sas ring member atoms; and wherein the cyclic groups A are unsubstitutedor substituted by 1 or 2 identical or different groups R^(A) as definedor preferably defined herein.

In a further preferred embodiment A is a 5-membered aromaticheterocycle, wherein the ring member atoms of the heterocycle includebesides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and Sas ring member atoms; and wherein the cyclic groups A are unsubstituted.

In one embodiment the invention relates to the use of compounds of theformula I, or the N-oxides, or the agriculturally acceptable saltsthereof for combating phytopathogenic harmful fungi, wherein the cyclicmoiety A is defined as in subformulae (A.1) to (A.12),

wherein #1 denotes the position which is bound to thetrifluoromethyloxadiazole moiety and #2 denotes the position, which isconnected to the —C(R³R⁴)—NR¹R² group of compounds of the formula I; andwherein the cyclic moiety A is unsubstituted or substituted by 1 or 2identical or different groups R^(A) and wherein R^(A) is as defined orpreferably defined herein. In another embodiment the cyclic moieties Aas defined in any one of subformulae (A.1) to (A.12) is unsubstituted orsubstituted by 1 or 2 identical or different groups R^(A); and whereinR^(A) is chlorine, fluorine or methyl. In a preferred embodiment thecyclic moiety A as defined in any one of subformulae (A.1) to (A.12) isunsubstituted.

In a preferred embodiment of the invention R^(A) is halogen, cyano,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl orC₃-C₈-cycloalkyl; and wherein any of the aliphatic and cyclic moietiesare unsubstituted or substituted by 1, 2, 3, 4 or up to the maximumpossible number of identical or different groups R^(a) as defined orpreferably defined herein.

In another preferred embodiment of the invention R^(A) is halogen,cyano, C₁-C₆-alkyl, C₁-C₆-alk-oxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl orC₃-C₈-cycloalkyl; and wherein any of the the aliphatic and cyclicmoieties are unsubstituted or substituted by 1, 2, 3, 4 or up to themaximum possible number of identical or different groups selected fromhalogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy and C₃-C₈-cycloalkyl; inparticular fluorine.

More preferably R^(A) is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; in particular halogen, C₁-C₆-alkyl;more particularly R^(A) is chlorine, fluorine or methyl.

In a more preferable embodiment R^(A) is chlorine, fluorine or methyl.

R^(a) according to the invention is halogen, cyano, NO₂, OH, SH, NH₂,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio or C₃-C₈-cycloalkyl. In a preferredembodiment of the invention R^(a) is halogen, cyano, C₁-C₆-alkyl,C₁-C₆-alkoxy or C₃-C₈-cycloalkyl. More preferably R^(a) is halogen, inparticular fluorine.

According to one embodiment R¹ is H. According to one embodiment R¹ isC₁-C₆-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl,i-butyl, t-butyl, in particular methyl, ethyl. According to a furtherembodiment R¹ is C₂-C₆-alkenyl, preferably ethylene. According to afurther embodiment R¹ is C₂-C₆-alkynyl, preferred ethynyl, 1-propynyl.According to a further embodiment R¹ is C₃-C₈-cycloalkyl, preferrablycyclopropyl, cyclobutyl, cyclopentyl, in particular cyclopropyl,cyclopentyl or cyclohexyl.

According to one embodiment R¹ is C₁-C₆-alkyl substituted by halogen,preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl,in particular methyl, ethyl. In a special embodiment of the invention R¹is CF₃.

According to one embodiment R¹ is C(═O)—(C₁-C₆-alkyl). According to oneembodiment R¹ is C(═O)—(C₁-C₆-alkyl), wherein alkyl is preferablymethyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, inparticular methyl, ethyl. According to one embodiment R¹ isC(═O)—(C₁-C₆-alkoxy), wherein alkoxy is preferrably methoxy, ethoxy,n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy. According to oneembodiment R¹ is phenyl-C₁-C₄-alkyl, wherein alkyl is preferably methyl,ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particularmethyl, ethyl.

According to one embodiment R¹ is heteroaryl-C₁-C₄-alkyl, wherein alkylis preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,t-butyl, in particular methyl, ethyl and wherein heteroaryl is furan,thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol,oxydiazol, pyrol, pyriminin.

According to one embodiment R¹ is phenyl. According to a furtherembodiment R¹ is benzyl.

According to a further embodiment R¹ is naphthyl. According to oneembodiment R¹ 3- to 10-membered saturated, partially unsaturated oraromatic mono- or bicyclic heterocycle, wherein the ring member atoms ofsaid mono- or bicyclic heterocycle include besides carbon atoms further1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atomsand wherein 1 or 2 carbon ring member atoms of the heterocycle may bereplaced by 1 or 2 groups independently selected from C(═O) and C(═S);and wherein the heteroaryl group in heteroaryl-C₁-C₄-alkyl is a 5- or6-membered aromatic heterocycle, wherein the ring member atoms of theheterocyclic ring include besides carbon atoms 1, 2, 3 or 4 heteroatomsselected from N, O and S as ring member atoms especially, furan,thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol,oxydiazol, pyrol, pyriminin.

According to a further embodiment the above mentioned groups may carryone, two, three or four identical or different substituents selectedfrom the group consisting of methyl, ethyl, propyl, butyl, preferablymethyl. According to a further embodiment the above mentioned groups maycarry one, two, three or four identical or different substituentsselected from the group consisting of partially or fully halogenatedmethyl, ethyl, propyl, butyl, preferably partially or fully halogenatedmethyl, in particular CF₃. According to a further embodiment the abovementioned groups may carry one, two, three or four identical ordifferent substituents selected from the group consisting of methoxy,ethoxy, propoxy, butoxy, preferably methoxy. According to a furtherembodiment the above mentioned groups may carry one, two, three or fouridentical or different substituents selected from the group consistingof partially or fully halogenated methoxy, ethoxy, propoxy, butoxy,preferably partially or fully halogenated methoxy, in particular OCF₃.In a special embodiment of the invention, R¹ is phenyl. In a furtherspecial embodiment of the invention, R¹ is phenyl substituted by Cl, F,Br, I, CH₃, OCH₃, CF₃ or OCF₃. In a further special embodiment of theinvention, R¹ is benzyl substituted by Cl, F, Br, I, CH₃, OCH₃, CF₃ orOCF₃. In a further special embodiment R¹ is naphtyl substituted by Cl,F, Br, I, CH₃, OCH₃, CF₃ or OCF₃. In a further special embodiment of theinvention, R¹ is thiophene substituted by Cl, F, Br, I, CH₃, OCH₃, CF₃or OCF₃. In a further special embodiment of the invention, R¹ is pyrolsubstituted by Cl, F, Br, I, CH₃, OCH₃, CF₃ or OCF₃. In a furtherspecial embodiment of the invention, R¹ is pyrazol substituted by Cl, F,Br, I, CH₃, OCH₃, CF₃ or OCF₃. In a further special embodiment of theinvention, R¹ is pyrimidin substituted by Cl, F, Br, I, CH₃, OCH₃, CF₃or OCF₃. In a further special embodiment of the invention, R¹ isoxydiazol substituted by Cl, F, Br, I, CHs, OCH₃, CF₃ or OCF₃.

In a preferred embodiment R¹ is H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl. In aspecial preferred embodiment R¹ is H, CHs, cyclopropyl.

According to one embodiment R² is H. According to one embodiment R² isC₁-C₆-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl,i-butyl, t-butyl, in particular methyl, ethyl. According to a furtherembodiment R² is C₂-C₆-alkenyl, preferably ethylene. According to afurther embodiment R² is C₂-C₆-alkynyl, preferred ethynyl, 1-propynyl.According to a further embodiment R² is C₃-C₈-cycloalkyl, preferrablycyclopropyl, cyclobutyl, cyclopentyl, in particular cyclopropyl,cyclopentyl or cyclohexyl.

According to one embodiment R² is C₁-C₆-alkyl substituted by halogen,preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl,in particular methyl, ethyl. In a special embodiment of the invention,R² is CF₃.

According to one embodiment R² is C(═O)—(C₁-C₆-alkyl). According to oneembodiment R² is C(═O)—(C₁-C₆-alkyl), wherein alkyl is preferablymethyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, inparticular methyl, ethyl. According to one embodiment R² isC(═O)—(C₁-C₆-alkoxy), wherein alkoxy is preferrably methoxy, ethoxy,n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy.

According to one embodiment R² is phenyl-C₁-C₄-alkyl, wherein alkyl ispreferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl,in particular methyl, ethyl.

According to one embodiment R² is heteroaryl-C₁-C₄-alkyl, wherein alkylis preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,t-butyl, in particular methyl, ethyl and wherein heteroaryl is furan,thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol,oxydiazol, pyrol, pyriminin.

According to one embodiment R² is phenyl. According to a furtherembodiment R² is benzyl. According to a further embodiment R² isnaphthyl. According to one embodiment R² is a 3- to 10-memberedsaturated, partially unsaturated or aromatic mono- or bicyclicheterocycle, wherein the ring member atoms of said mono- or bicyclicheterocycle include besides carbon atoms further 1, 2, 3 or 4heteroatoms selected from N, O and S as ring member atoms and wherein 1or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or2 groups independently selected from C(═O) and C(═S); and wherein theheteroaryl group in heteroaryl-C₁-C₄-alkyl is a 5- or 6-memberedaromatic heterocycle, wherein the ring member atoms of the heterocyclicring include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected fromN, O and S as ring member atoms especially, furan, thiophen, pyrazol,isoxazol, imidazole, oxazol, thiazol, triazol, oxydiazol, pyrol,pyrimidin.

According to a further embodiment the above mentioned groups may carryone, two, three or four identical or different substituents selectedfrom the group consisting of methyl, ethyl, propyl, butyl, preferablymethyl. According to a further embodiment the above mentioned groups maycarry one, two, three or four identical or different substituentsselected from the group consisting of partially or fully halogenatedmethyl, ethyl, propyl, butyl, preferably partially or fully halogenatedmethyl, in particular CF₃. According to a further embodiment the abovementioned groups may carry one, two, three or four identical ordifferent substituents selected from the group consisting of methoxy,ethoxy, propoxy, butoxy, preferably methoxy. According to a furtherembodiment the above mentioned groups may carry one, two, three or fouridentical or different substituents selected from the group consistingof partially or fully halogenated methoxy, ethoxy, propoxy, butoxy,preferably partially or fully halogenated methoxy, in particular OCF₃.In a special embodiment of the invention, R² is phenyl. In a furtherspecial embodiment of the invention, R² is phenyl substituted by Cl, F,Br, I, CH₃, OCH₃, CF₃ or OCF₃. In a further special embodiment of theinvention, R² is benzyl substituted by Cl, F, Br, I, CH₃, OCH₃, CF₃ orOCF₃. In a further special embodiment R² is naphtyl substituted by Cl,F, Br, I, CH₃, OCH₃, CF₃ or OCF₃. In a further special embodiment of theinvention, R² is thiophene substituted by Cl, F, Br, I, CH₃, OCH₃, CF₃or OCF₃. In a further special embodiment of the invention, R² is pyrolsubstituted by Cl, F, Br, I, CH₃, OCH₃, CF₃ or OCF₃. In a furtherspecial embodiment of the invention, R² is pyrazol substituted by Cl, F,Br, I, CH₃, OCH₃, CF₃ or OCF₃. In a further special embodiment of theinvention, R² is pyrimidin substituted by Cl, F, Br, I, CH₃, OCH₃, CF₃or OCF₃. In a further special embodiment of the invention, R² isoxydiazol substituted by Cl, F, Br, I, CH₃, OCH₃, CF₃ or OCF₃.

In a preferred embodiment R² is H, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, phenyl-C₁-C₄-alkyl,heteroaryl-C₁-C₄-alkyl, phenyl. In a special preferred embodiment R² isH, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, phenyl-C₁-C₄-alkyl,heteroaryl-C₁-C₄-alkyl, phenyl. In a further special preferredembodiment R² is H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, phenyl-C₁-C₄-alkyl,phenyl. In a further special preferred embodiment R² is H, CH₃, CH₂CH₃,cyclopropyl, phenyl, benzyl. In another preferred embodiment R¹ ishydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, phenyl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl, phenylor a 3- to 10-membered saturated, partially unsaturated mono- orbicyclic heterocycle, wherein the ring member atoms of said mono- orbicyclic heterocycle include besides carbon atoms further 1, 2, 3 or 4heteroatoms selected from N, O and S as ring member atoms and wherein 1or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or2 groups independently selected from C(═O) and C(═S); and wherein theheteroaryl group in heteroaryl-C₁-C₄-alkyl is a 5- or 6-memberedaromatic heterocycle, wherein the ring member atoms of the heterocyclicring include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected fromN, O and S as ring member atoms; and wherein any of the above-mentionedaliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3or up to the maximum possible number of identical or different groupsR^(1a); wherein R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, NHSO₂—C₁-C₄-alkyl,(C═O)—(C₁-C₄-alkyl), C(═O)—(C₁-C₄-alkoxy) or C₁-C₆-alkylsulfonyl; andwherein R² is C(═O)—(C₁-C₆-alkyl) or C(═O)—(C₁-C₆-alkoxy). In a furtherembodiment R¹ and R² independently of each other are hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C(═O)—(C₁-C₆-alkyl), C(═O)—(C₁-C₆-alkoxy), phenyl-C₁-C₄-alkyl or phenyl;and wherein the aliphatic and the cyclic groups are unsubstituted orsubstituted by 1, 2, 3, 4 or up to the maximum possible number ofidentical or different groups R^(1a) as defined herein.

In another embodiment R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl orC₂-C₆-alkynyl and R² is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, phenyl-C₁-C₄-alkyl,heteroaryl-C₁-C₄-alkyl, phenyl or heteroaryl; and wherein the heteroarylgroup is a 5- or 6-membered aromatic heterocycle, wherein the ringincludes besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N,O and S as ring member atoms; and wherein any of the aliphatic or cyclicgroups are unsubstituted or substituted by 1, 2, 3, 4 or up to themaximum possible number of identical or different groups R^(1a) asdefined or preferably defined herein.

In one aspect of the invention R¹ and R² independently of each other arehydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C(═O)—(C₁-C₆-alkyl) or C(═O)—(C₁-C₆-alkoxy); and wherein any of thealiphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3,4 or up to the maximum possible number of identical or different groupsR^(1a) as defined or preferably defined herein.

In another embodiment R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl or C₃-C₈-cycloalkyl and R² is C(═O)—(C₁-C₆-alkyl) orC(═O)—(C₁-C₆-alkoxy); and wherein any of the aliphatic or cyclic groupsare unsubstituted or substituted by 1, 2, 3, 4 or up to the maximumpossible number of identical or different groups R^(1a) as defined orpreferably defined herein.

In another embodiment R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl or C₃-C₈-cycloalkyl and R² is C(═O)—(C₁-C₆-alkyl); andwherein any of the aliphatic or cyclic groups are unsubstituted orsubstituted by 1, 2, 3, 4 or up to the maximum possible number ofidentical or different radicals selected from the group fluorine,chlorine and methyl.

In one aspect of the invention R¹ and R² independently of each other arehydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl;and wherein any of the aliphatic or cyclic groups are unsubstituted orsubstituted by 1, 2, 3, 4 or up to the maximum possible number ofidentical or different groups R^(1a) as defined or preferably definedherein.

In a further aspect of the invention R¹ is hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl and R² is phenyl-C₁-C₄-alkyl,heteroaryl-C₁-C₄-alkyl, phenyl or heteroaryl; and wherein the heteroarylgroup is a 5- or 6-membered aromatic heterocycle wherein the ringincludes besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N,O and S as ring member atoms; and wherein any of the aliphatic or cyclicgroups are unsubstituted or substituted by 1, 2, 3, 4 or up to themaximum possible number of identical or different groups R^(1a) asdefined or preferably defined herein.

In a further aspect of the invention R¹ is hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl and R² is phenyl-C₁-C₄-alkyl,heteroaryl-C₁-C₄-alkyl or phenyl; and wherein the heteroaryl group is a5- or 6-membered aromatic heterocycle wherein the ring includes besidescarbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ringmember atoms; and wherein any of the aliphatic or cyclic groups areunsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possiblenumber of identical or different groups R^(1a) as defined or preferablydefined herein.

In one embodiment R¹ is hydrogen or C₁-C₄-alkyl and R² isC₃-C₈-cycloalkyl, wherein the cycloalkyl group is unsubstituted orcarries 1, 2, 3, 4 or up to the maximum possible number of identical ordifferent groups R^(1a) as defined or preferably defined herein.

In one embodiment R¹ is hydrogen or C₁-C₄-alkyl and R² is C₁-C₆-alkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl, wherein the aliphatic groups areunsubstituted or carry 1, 2, 3, 4 or up to the maximum possible numberof identical or different groups R^(1a) as defined or preferably definedherein.

In one embodiment R¹ is hydrogen or C₁-C₄-alkyl and R² is phenyl, a 5-or 6-membered aromatic heterocycle, phenyl-C₁-C₄-alkyl orheteroaryl-C₁-C₄-alkyl, wherein the ring member atoms of theheterocyclic ring include besides carbon atoms 1, 2, 3 or 4 heteroatomsselected from N, O and S as ring member atoms; and wherein any of thecyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up tothe maximum possible number of identical or different groups R^(1a) asdefined or preferably defined herein.

In one embodiment R¹ is hydrogen or C₁-C₄-alkyl and R² isphenyl-C₁-C₄-alkyl or heteroaryl-C₁-C₄-alkyl; wherein the heteroarylgroup is a 5- or 6-membered aromatic heterocycle, wherein the ringmember atoms of the aromatic heterocycle include besides carbon atoms 1,2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms;wherein any of the aliphatic or cyclic groups are unsubstituted orsubstituted by 1, 2, 3, 4 or up to the maximum possible number ofidentical or different groups R^(1a) as defined or preferably definedherein.

In one embodiment R¹ is hydrogen or C₁-C₄-alkyl and R² is phenyl or a 5-or 6-membered aromatic heterocycle, wherein the ring member atoms of theheterocyclic ring include besides carbon atoms 1, 2, 3 or 4 heteroatomsselected from N, O and S as ring member atoms; and wherein any of thecyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up tothe maximum possible number of identical or different groups R^(1a) asdefined or preferably defined herein.

In one embodiment of the invention R¹ and R² together with the nitrogenatom to which they are bound form a saturated or partially unsaturatedmono- or bicyclic 3- to 7-membered heterocycle, wherein the heterocycleincludes beside one nitrogen atom and one or more carbon atoms 1, 2 or 3heteroatoms independently selected from N, O and S as ring member atoms;and wherein one or two CH₂ groups of the heterocycle may be replaced byone or two groups independently selected from the group of C(═O) andC(═S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3,4 or up to the maximum possible number of identical or different groupsR^(1a); wherein R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, NHSO₂—C₁-C₄-alkyl,(C═O)—C₁-C₄-alkyl, C(═O)—C₁-C₄-alkoxy or C₁-C₆-alkylsulfonyl.

In one embodiment of the invention R¹ and R² together with the N atom towhich it is bound form a saturated or partially unsaturated 3- to6-membered heterocycle, wherein the heterocycle includes beside onenitrogen atom and one or more carbon atoms no further heteroatoms.

In one embodiment of the invention R¹ and R² together with the N towhich it is bound form a saturated or partially unsaturated 3- to6-membered heterocycle, wherein one or two CH₂ groups of the heterocyclemay be replaced by one or two groups independently selected from thegroup of C(═O) and C(═S). In one embodiment R¹ and R² together with thenitrogen atom to which they are bound form a saturated or partiallyunsaturated monocyclic 5- to 7-membered heterocycle, wherein theheterocycle includes beside one nitrogen atom and one or more carbonatoms no further heteroatom or 1 or 2 heteroatoms independently selectedfrom N, O and S as ring member atoms; and wherein one or two CH₂ groupsof the heterocycle may be replaced by one or two groups independentlyselected from the group of C(═O) and C(═S); and wherein the heterocycleis unsubstituted or carries 1, 2, 3, 4 or up to the maximum possiblenumber of identical or different groups R^(1a) as defined or preferablydefined herein; particularly R^(1a) is halogen or C₁-C₆-alkyl.

In a further embodiment R¹ and R² together with the nitrogen atom towhich they are bound form a saturated or partially unsaturatedmonocyclic 5- or 6-membered heterocycle, wherein the heterocycleincludes beside one nitrogen atom and one or more carbon atoms nofurther heteroatom or 1 further heteroatom independently selected fromN, O and S as ring member atoms; and wherein one or two CH₂ groups ofthe heterocycle may be replaced by one or two groups independentlyselected from the group of C(═O) and C(═S); and wherein the heterocycleis unsubstituted or carries 1, 2, 3, 4 or up to the maximum possiblenumber of identical or different groups R^(1a) as defined or preferablydefined herein; particularly R^(1a) is halogen or

In one embodiment of the invention R^(1a) is halogen, cyano,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy. In another preferredaspect of the invention R^(1a) is fluorine, chlorine, cyano, methyl,methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl ordifluoromethoxy. In a more preferred aspect of the invention R^(1a) ishalogen or C₁-C₆-alkyl; particularly fluorine, chlorine or methyl.

In one special preferred embodiment of the invention R¹ and R² togetherwith the N atom to which it is bound form a aziridinyl.

In one special preferred embodiment of the invention R¹ and R² togetherwith the N atom to which it is bound form a azetidinyl.

In one special preferred embodiment of the invention R¹ and R² togetherwith the N atom to which it is bound form a 1-pyrrolidinyl.

In one special preferred embodiment of the invention R¹ and R² togetherwith the N atom to which it is bound form a 1-piperidinyl.

In one special preferred embodiment of the invention R¹ and R² togetherwith the N atom to which it is bound form a 1-piperazinyl.

In one special preferred embodiment of the invention R¹ and R² togetherwith the N atom to which it is bound form a 1-methyl-4-piperazinyl.

In one special preferred embodiment of the invention R¹ and R² togetherwith the N atom to which it is bound form a 4-morpholinyl.

In one embodiment of the invention R^(1a) is halogen, cyano,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy. In another preferredaspect of the invention R^(1a) is fluorine, chlorine, cyano, methyl,methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl ordifluoromethoxy. In a more preferred aspect of the invention R^(1a) ishalogen or C₁-C₆-alkyl; particularly fluorine, chlorine or methyl.

According to one embodiment R³ is H. According to one embodiment R³ isC₁-C₆-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl,i-butyl, t-butyl, in particular methyl, ethyl.

According to one embodiment R³ is C₁-C₆-haloalkyl, preferably by halogensubstituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,t-butyl, in particular methyl, ethyl. In a preferred embodiment of theinvention, R³ is H, CH₃ and CF₃. In a special embodiment of theinvention, R³ is CF₃.

According to one embodiment R⁴ is H. According to one embodiment R⁴ isC₁-C₆-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl,i-butyl, t-butyl, in particular methyl, ethyl.

According to one embodiment R⁴ is C₁-C₆-haloalkyl, preferably by halogensubstituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,t-butyl, in particular methyl, ethyl. In a preferred embodiment of theinvention, R⁴ is H, CH₃ and CF₃. In a special embodiment of theinvention, R⁴ is CF₃.

According to one embodiment R³ and R⁴ are independently of each otherhydrogen, fluorine, methyl or trifluoromethyl. In a further embodimentR³ and R⁴ are independently selected from the group consisting ofhydrogen and C₁-C₄-alkyl, in particular from hydrogen and CH₃. Accordingto another embodiment R³ is hydrogen and R⁴ is hydrogen or C₁-C₄-alkyl,in particular hydrogen or CH₃.

In another aspect R³ and R⁴ are both hydrogen. In a further aspect R³ ishydrogen and R⁴ is CH₃. In still another aspect R³ is hydrogen and R⁴ istrifluoromethyl. In yet another aspect R³ and R⁴ are both methyl. In oneembodiment R³ and R⁴ are both trifluoromethyl.

In yet another embodiment R³ and R⁴ independently of each other are H,CH₃ or trifluoromethyl.

In one embodiment the present invention relates to compounds (1.1) ofthe formula I wherein:

-   A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the    ring member atoms of the heterocyclic ring include besides carbon    atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring    member atoms; and wherein the cyclic groups A are unsubstituted or    substituted by 1, 2, 3 or 4 identical or different groups R^(A);    wherein    -   R^(A) is halogen, cyano, NO₂, OH, NH₂, SH, C₁-C₆-alkoxy,        C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy; and        wherein any of the aliphatic or cyclic moieties are        unsubstituted or substituted by 1, 2, 3 or 4 identical or        different groups R^(a); wherein        -   R^(a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₁-C₆-haloalkylthio or C₃-C₈-cycloalkyl;-   R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, heteroaryl-C₁-C₄-alkyl,    phenyl, naphthyl or a 3- to 10-membered saturated, partially    unsaturated or aromatic mono- or bicyclic heterocycle, wherein the    ring member atoms of said mono- or bicyclic heterocycle include    besides carbon atoms further 1, 2, 3 or 4 heteroatoms selected from    N, O and S as ring member atoms and wherein 1 or 2 carbon ring    member atoms of the heterocycle may be replaced by 1 or 2 groups    independently selected from C(═O) and C(═S); and wherein the    heteroaryl group in heteroaryl-C₁-C₄-alkyl is a 5- or 6-membered    aromatic heterocycle, wherein the ring member atoms of the    heterocyclic ring include besides carbon atoms 1, 2, 3 or 4    heteroatoms selected from N, O and S as ring member atoms; and    wherein any of the above-mentioned aliphatic or cyclic groups are    unsubstituted or substituted by 1, 2, 3 or up to the maximum    possible number of identical or different groups R^(1a); wherein    -   R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, NHSO₂—C₁-C₄-alkyl, (C═O)—C₁-C₄-alkyl,        C(═O)—C₁-C₄-alkoxy, C₁-C₆-alkylsulfonyl or        C₁-C₆-haloalkylsulfonyl;-   R² is C(═O)—(C₁-C₆-alkyl), C(═O)—(C₁-C₆-alkoxy);-   or R¹ and R² together with the nitrogen atom to which they are bound    form a saturated or partially unsaturated mono- or bicyclic 3- to    7-membered heterocycle, wherein the heterocycle includes beside one    nitrogen atom and one or more carbon atoms no further heteroatom or    1, 2 or 3 further heteroatoms independently selected from N, O and S    as ring member atoms; and wherein one or two CH₂ groups of the    heterocycle may be replaced by one or two groups independently    selected from the group of C(═O) and C(═S); and wherein the    heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the    maximum possible number of identical or different groups R^(1a) as    defined or preferably defined herein;-   R³ is H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;-   R⁴ is H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;-   or the N-oxides, or the agriculturally acceptable salts thereof.

In a further embodiment the invention relates to compounds (I.1),wherein A is (A.2). In a further embodiment the invention relates tocompounds (I.1), wherein A is (A.2), and wherein A is substituted by 1group R^(A) as defined or preferably defined herein. In yet anotherembodiment the invention relates to compounds (I.1), wherein A is (A.2),and wherein A is unsubstituted. In another embodiment the inventionrelates to compounds (I.1), wherein A is (A.8). In a further embodimentthe invention relates to compounds (I.1), wherein A is (A.8), andwherein A is substituted by 1 group R^(A) as defined or preferablydefined herein. In yet another embodiment the invention relates tocompounds (I.1), wherein A is (A.8), and wherein A is unsubstituted. Inanother embodiment the invention relates to compounds (I.1), wherein Ais (A.4). In a further embodiment the invention relates to compounds(I.1), wherein A is (A.4), and wherein A is substituted by 1 group R^(A)as defined or preferably defined herein. In yet another embodiment theinvention relates to compounds (I.1), wherein A is (A.4), and wherein Ais unsubstituted.

In one embodiment the present invention relates to compounds (I.2) ofthe formula I wherein:

-   A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the    ring member atoms of the heterocyclic ring include besides carbon    atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring    member atoms; and wherein the cyclic groups A are unsubstituted or    substituted by 1, 2, 3 or 4 identical or different groups R^(A);    wherein    -   R^(A) is halogen, cyano, NO₂, OH, NH₂, SH, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,        C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy; and wherein any of the        aliphatic or cyclic moieties are unsubstituted or substituted by        1, 2, 3 or 4 identical or different groups R^(a); wherein        -   R^(a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₁-C₆-alkylthio, C₁-C₆-haloalkylthio or C₃-C₈-cycloalkyl;-   R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, phenyl-C₁-C₄-alkyl,    heteroaryl-C₁-C₄-alkyl, phenyl or a 3- to 10-membered saturated,    partially unsaturated mono- or bicyclic heterocycle, wherein the    ring member atoms of said mono- or bicyclic heterocycle include    besides carbon atoms further 1, 2, 3 or 4 heteroatoms selected from    N, O and S as ring member atoms and wherein 1 or 2 carbon ring    member atoms of the heterocycle may be replaced by 1 or 2 groups    independently selected from C(═O) and C(═S); and wherein the    heteroaryl group in heteroaryl-C₁-C₄-alkyl is a 5- or 6-membered    aromatic heterocycle, wherein the ring member atoms of the    heterocyclic ring include besides carbon atoms 1, 2, 3 or 4    heteroatoms selected from N, O and S as ring member atoms; and    wherein any of the above-mentioned aliphatic or cyclic groups are    unsubstituted or substituted by 1, 2, 3 or up to the maximum    possible number of identical or different groups R^(1a); wherein    -   R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,        NHSO₂—C₁-C₄-alkyl, (C═O)—C₁-C₄-alkyl, C(═O)—C₁-C₄-alkoxy or        C₁-C₆-alkylsulfonyl;-   R² is C(═O)—(C₁-C₆-alkyl) or C(═O)—(C₁-C₆-alkoxy);-   or R¹ and R² together with the nitrogen atom to which they are bound    form a saturated or partially unsaturated monocyclic 5- to    7-membered heterocycle, wherein the heterocycle includes beside one    nitrogen atom and one or more carbon atoms no further heteroatom or    1 or 2 further heteroatoms independently selected from N, O and S as    ring member atoms; and wherein one or two CH₂ groups of the    heterocycle are replaced by one or two groups independently selected    from the group of C(═O) and C(═S); and wherein the heterocycle is    unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible    number of identical or different groups R^(1a) as defined or    preferably defined herein; particularly R^(1a) is halogen or    C₁-C₆-alkyl;-   R³, R⁴ independently of each other are hydrogen, C₁-C₄-alkyl or    C₁-C₄-haloalky;-   or the N-oxides, or the agriculturally acceptable salts thereof.

In a further embodiment the invention relates to compounds (I.2),wherein A is (A.2). In a further embodiment the invention relates tocompounds (I.2), wherein A is (A.2), and wherein A is substituted by 1group R^(A) as defined or preferably defined herein. In yet anotherembodiment the invention relates to compounds (I.2), wherein A is (A.2),and wherein A is unsubstituted. In another embodiment the inventionrelates to compounds (I.2), wherein A is (A.8). In a further embodimentthe invention relates to compounds (I.2), wherein A is (A.8), andwherein A is substituted by 1 group R^(A) as defined or preferablydefined herein. In yet another embodiment the invention relates tocompounds (I.2), wherein A is (A.8), and wherein A is unsubstituted. Inanother embodiment the invention relates to compounds (I.2), wherein Ais (A.4). In another embodiment the invention relates to compounds(I.2), wherein A is (A.4), and wherein R⁴ is hydrogen or CH₃. In afurther embodiment the invention relates to compounds (I.2), wherein Ais (A.4), and wherein A is substituted by 1 group R^(A) as defined orpreferably defined herein. In a further embodiment the invention relatesto compounds (I.2), wherein A is (A.4), and wherein A is substituted by1 group R^(A) as defined or preferably defined herein, and wherein R³ ishydrogen and R⁴ is hydrogen or CH₃. In yet another embodiment theinvention relates to compounds (I.2), wherein A is (A.4), and wherein Ais unsubstituted. In yet another embodiment the invention relates tocompounds (I.2), wherein A is (A.4), and wherein A is unsubstituted, andwherein R³ is hydrogen and wherein R⁴ is hydrogen or CH₃.

In one embodiment the present invention relates to compounds (I.3) ofthe formula I wherein:

-   A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the    ring member atoms of the heterocyclic ring include besides carbon    atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring    member atoms; and wherein the cyclic groups A are unsubstituted or    substituted by 1, 2, 3 or 4 identical or different groups R^(A);    wherein    -   R^(A) is halogen, cyano, NO₂, OH, NH₂, SH, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,        C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy; and wherein any of the        aliphatic or cyclic moieties are unsubstituted or substituted by        1, 2, 3 or 4 identical or different groups R^(a); wherein        -   R^(a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₁-C₆-alkylthio, C₁-C₆-haloalkylthio or C₃-C₈-cycloalkyl;-   R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or    C₃-C₈-cycloalkyl;-   R² is C(═O)—(C₁-C₆-alkyl) or C(═O)—(C₁-C₆-alkoxy);-   R³ is hydrogen;-   R⁴ is hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalky;-   or the N-oxides, or the agriculturally acceptable salts thereof.

In a further embodiment the invention relates to compounds (I.3),wherein A is (A.2). In a further embodiment the invention relates tocompounds (I.3), wherein A is (A.2), and wherein A is substituted by 1group R^(A) as defined or preferably defined herein. In yet anotherembodiment the invention relates to compounds (I.3), wherein A is (A.2),and wherein A is unsubstituted. In another embodiment the inventionrelates to compounds (I.3), wherein A is (A.8). In a further embodimentthe invention relates to compounds (I.3), wherein A is (A.8), andwherein A is substituted by 1 group R^(A) as defined or preferablydefined herein. In yet another embodiment the invention relates tocompounds (I.3), wherein A is (A.8), and wherein A is unsubstituted. Inanother embodiment the invention relates to compounds (I.3), wherein Ais (A.4). In another embodiment the invention relates to compounds(I.3), wherein A is (A.4), and wherein R⁴ is hydrogen or CH₃. In afurther embodiment the invention relates to compounds (I.3), wherein Ais (A.4), and wherein A is substituted by 1 group R^(A) as defined orpreferably defined herein. In a further embodiment the invention relatesto compounds (I.3), wherein A is (A.4), and wherein A is substituted by1 group R^(A) as defined or preferably defined herein, and wherein R⁴ ishydrogen or CH₃. In yet another embodiment the invention relates tocompounds (I.3), wherein A is (A.4), and wherein A is unsubstituted. Inyet another embodiment the invention relates to compounds (I.3), whereinA is (A.4), and wherein A is unsubstituted, and wherein R⁴ is hydrogenor CH₃.

In one embodiment the present invention relates to compounds (I.4) ofthe formula I wherein:

-   A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the    ring member atoms of the heterocyclic ring include besides carbon    atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring    member atoms; and wherein the cyclic groups A are unsubstituted or    substituted by 1, 2, 3 or 4 identical or different groups R^(A);    wherein    -   R^(A) is chlorine, fluorine or methyl;-   R¹ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or    C₃-C₈-cycloalkyl;-   R² is C(═O)—(C₁-C₆-alkyl) or C(═O)—(C₁-C₆-alkoxy);-   R³ is hydrogen;-   R⁴ is hydrogen or CH₃;-   or the N-oxides, or the agriculturally acceptable salts thereof.

In a further embodiment the invention relates to compounds (I.4),wherein A is (A.2). In a further embodiment the invention relates tocompounds (I.4), wherein A is (A.2), and wherein A is substituted by 1group R^(A) as defined or preferably defined herein. In yet anotherembodiment the invention relates to compounds (I.4), wherein A is (A.2),and wherein A is unsubstituted.

In another embodiment the invention relates to compounds (I.4), whereinA is (A.8). In a further embodiment the invention relates to compounds(I.4), wherein A is (A.8), and wherein A is substituted by 1 group R^(A)as defined or preferably defined herein. In yet another embodiment theinvention relates to compounds (I.4), wherein A is (A.8), and wherein Ais unsubstituted. In another embodiment the invention relates tocompounds (I.4), wherein A is (A.4). In a further embodiment theinvention relates to compounds (I.4), wherein A is (A.4), and wherein Ais substituted by 1 group R^(A) as defined or preferably defined herein.In yet another embodiment the invention relates to compounds (I.4),wherein A is (A.4), and wherein A is unsubstituted.

In one embodiment the present invention relates to compounds (I.5) ofthe formula I wherein:

-   A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the    ring member atoms of the heterocyclic ring include besides carbon    atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring    member atoms; and wherein the cyclic groups A are unsubstituted or    substituted by 1, 2, 3 or 4 identical or different groups R^(A);    wherein    -   R^(A) is halogen, cyano, NO₂, OH, NH₂, SH, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,        C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy; and wherein any of the        aliphatic or cyclic moieties are unsubstituted or substituted by        1, 2, 3 or 4 identical or different groups R^(a); wherein        -   R^(a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₁-C₆-alkylthio, C₁-C₆-haloalkylthio or C₃-C₈-cycloalkyl;-   R¹ and R² together with the nitrogen atom to which they are bound    form a saturated or partially unsaturated monocyclic 5- to    7-membered heterocycle, wherein the heterocycle includes beside one    nitrogen atom and one or more carbon atoms no further heteroatom or    1 or 2 further heteroatoms independently selected from N, O and S as    ring member atoms; and wherein one or two CH₂ groups of the    heterocycle are replaced by one or two groups independently selected    from the group of C(═O) and C(═S); and wherein the heterocycle is    unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible    number of identical or different groups R^(1a) as defined or    preferably defined herein; particularly R^(1a) is halogen or    C₁-C₆-alkyl;-   R³, R⁴ independently of each other are hydrogen, C₁-C₄-alkyl or    C₁-C₄-haloalky; or the N-oxides, or the agriculturally acceptable    salts thereof.

In a further embodiment the invention relates to compounds (I.5),wherein A is (A.2). In a further embodiment the invention relates tocompounds (I.5), wherein A is (A.2), and wherein A is substituted by 1group R^(A) as defined or preferably defined herein. In yet anotherembodiment the invention relates to compounds (I.5), wherein A is (A.2),and wherein A is unsubstituted. In another embodiment the inventionrelates to compounds (I.5), wherein A is (A.8). In a further embodimentthe invention relates to compounds (I.5), wherein A is (A.8), andwherein A is substituted by 1 group R^(A) as defined or preferablydefined herein. In yet another embodiment the invention relates tocompounds (I.5), wherein A is (A.8), and wherein A is unsubstituted. Inanother embodiment the invention relates to compounds (I.5), wherein Ais (A.4). In another embodiment the invention relates to compounds(I.5), wherein A is (A.4), and wherein R⁴ is hydrogen or CH₃. In afurther embodiment the invention relates to compounds (I.5), wherein Ais (A.4), and wherein A is substituted by 1 group R^(A) as defined orpreferably defined herein. In a further embodiment the invention relatesto compounds (I.5), wherein A is (A.4), and wherein A is substituted by1 group R^(A) as defined or preferably defined herein, and wherein R³ ishydrogen and R⁴ is hydrogen or CH₃. In yet another embodiment theinvention relates to compounds (I.5), wherein A is (A.4), and wherein Ais unsubstituted. In yet another embodiment the invention relates tocompounds (I.5), wherein A is (A.4), and wherein A is unsubstituted, andwherein R³ is hydrogen and wherein R⁴ is hydrogen or CH₃.

In one embodiment the present invention relates to compounds (I.6) ofthe formula I wherein:

-   A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the    ring member atoms of the heterocyclic ring include besides carbon    atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring    member atoms; and wherein the cyclic groups A are unsubstituted or    substituted by 1, 2, 3 or 4 identical or different groups R^(A);    wherein    -   R^(A) is halogen, cyano, NO₂, OH, NH₂, SH, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,        C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy; and wherein any of the        aliphatic or cyclic moieties are unsubstituted or substituted by        1, 2, 3 or 4 identical or different groups R^(a); wherein        -   R^(a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₁-C₆-alkylthio, C₁-C₆-haloalkylthio or C₃-C₈-cycloalkyl;-   R¹ and R² together with the nitrogen atom to which they are bound    form a saturated or partially unsaturated monocyclic 5- or    6-membered heterocycle, wherein the heterocycle includes beside one    nitrogen atom and one or more carbon atoms no further heteroatom or    1 further heteroatom independently selected from N, O and S as ring    member atoms; and wherein one or two CH₂ groups of the heterocycle    are replaced by one or two groups independently selected from the    group of C(═O) and C(═S); and wherein the heterocycle is    unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible    number of identical or different groups R^(1a) as defined or    preferably defined herein; particularly R^(1a) is halogen or    C₁-C₆-alkyl;-   R³ is hydrogen;-   R⁴ is hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;-   or the N-oxides, or the agriculturally acceptable salts thereof.

In a further embodiment the invention relates to compounds (I.6),wherein A is (A.2). In a further embodiment the invention relates tocompounds (I.6), wherein A is (A.2), and wherein A is substituted by 1group R^(A) as defined or preferably defined herein. In yet anotherembodiment the invention relates to compounds (I.6), wherein A is (A.2),and wherein A is unsubstituted. In another embodiment the inventionrelates to compounds (I.6), wherein A is (A.8). In a further embodimentthe invention relates to compounds (I.6), wherein A is (A.8), andwherein A is substituted by 1 group R^(A) as defined or preferablydefined herein. In yet another embodiment the invention relates tocompounds (I.6), wherein A is (A.8), and wherein A is unsubstituted. Inanother embodiment the invention relates to compounds (I.6), wherein Ais (A.4). In another embodiment the invention relates to compounds(I.6), wherein A is (A.4), and wherein R⁴ is hydrogen or CH₃. In afurther embodiment the invention relates to compounds (I.6), wherein Ais (A.4), and wherein A is substituted by 1 group R^(A) as defined orpreferably defined herein. In a further embodiment the invention relatesto compounds (I.6), wherein A is (A.4), and wherein A is substituted by1 group R^(A) as defined or preferably defined herein, and wherein R⁴ ishydrogen or CH₃. In yet another embodiment the invention relates tocompounds (I.6), wherein A is (A.4), and wherein A is unsubstituted. Inyet another embodiment the invention relates to compounds (I.6), whereinA is (A.4), and wherein A is unsubstituted, and wherein R⁴ is hydrogenor CH₃.

According to one embodiment, the present invention relates to compoundsof the formula I.A

or to the use of the compounds of the formula I.A for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.B

or to the use of the compounds of the formula I.B for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.C

or to the use of the compounds of the formula I.C for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.D

or to the use of the compounds of the formula I.D for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.E

or to the use of the compounds of the formula I.E for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.F

or to the use of the compounds of the formula I.F for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.G

or to the use of the compounds of the formula I.G for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.H

or to the use of the compounds of the formula I.H for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.I

or to the use of the compounds of the formula I.I for controllingphytopathogenic fungi. Here, the variables are as defined elsewhereherein for formula I, or as defined as being preferred for formula I.

According to one embodiment, the present invention relates to compoundsof the formula I.J or to the use of the compounds of the formula I.J forcontrolling phytopathogenic fungi. Here, the variables are as definedelsewhere herein for formula I, or as defined as being preferred forformula I.

According to one embodiment, the present invention relates to compoundsof the formula I.K, I.L, I.M, I.N, I.O, I.P, I.Q, I.R or I.S or to theuse of the compounds of the formula I.K, I.L, I.M, I.N, I.O, I.P, I.Q,I.R or I.S for controlling phytopathogenic fungi. Here, the variables R³and R⁴ are as defined or preferably defined herein for formula I.

Preference is given to the compounds I used according to the inventionand to the compounds according to the invention compiled in Tables 1 to10 below. With regard to the compounds according to the invention theexception as defined above will be considered. The groups mentioned fora substituent in the tables are furthermore per se, independently of thecombination in which they are mentioned, a particularly preferred aspectof the substituent in question.

Table 1

Compounds of the formula I.A, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.A.A-1 toI.A.A-973). For example, compound I.A.A-3 is therefore to be construedas a compound of formula I.A, wherein the meaning of R¹ and R² is asdefined in line A-3 of table A (R¹ is hydrogen and R² is ethyl).

Table 2

Compounds of the formula I.B, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.B.A-1 toI.B.A-973).

Table 3

Compounds of the formula I.C, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.C.A-1 toI.C.A-973)

Table 4

Compounds of the formula I.D, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.D.A-1 toI.D.A-973).

Table 5

Compounds of the formula I.E, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.E.A-1 toI.E.A-973).

Table 6

Compounds of the formula I.F, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.F.A-1 toI.F.A-973).

Table 7

Compounds of the formula I.G, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.G.A-1 toI.G.A-503).

Table 8

Compounds of the formula I.H, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.H.A-1 toI.H.A-973).

Table 9

Compounds of the formula I.I, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.I.A-1 toI.I.A-973).

Table 10

Compounds of the formula I.J, in which R¹ and R² for each individualcompound corresponds in each case to one line of Table A (I.J.A-1 toI.J.A-973).

TABLE A No R¹ R² A-1 H H A-2 H CH₃ A-3 H CH₂CH₃ A-4 H CH₂CH₂CH₃ A-5 HCH(CH₃)₂ A-6 H CH₂CH₂CH₂CH₃ A-7 H CH(CH₃)CH₂CH₃ A-8 H CH₂CH(CH₃)CH₃ A-9H C(CH₃)₃ A-10 H C(═O)—CH₃ A-11 H C(═O)—CH₂CH₃ A-12 H C(═O)—CH₂CH₂CH₃A-13 H C(═O)—CH(CH₃)₂ A-14 H C(═O)—CH₂CH₂CH₂CH₃ A-15 HC(═O)—CH(CH₃)CH₂CH₃ A-16 H C(═O)—CH₂CH(CH₃)CH₃ A-17 H C(═O)—C(CH₃)₃ A-18H C(═O)—CH₂CH₂CH₂CH₂CH₃ A-19 H C(═O)—CH(CH₃)CH₂CH₂CH₃ A-20 HC(═O)—CH₂CH(CH₃)CH₂CH₃ A-21 H C(═O)—CH₂CH₂CH(CH₃)CH₃ A-22 HC(═O)—CH(CH₂CH₃)CH₂CH₃ A-23 H C(═O)—OCH₃ A-24 H C(═O)—OCH₂CH₃ A-25 HC(═O)—OCH₂CH₂CH₃ A-26 H C(═O)—OCH(CH₃)₂ A-27 H C(═O)—OCH₂CH₂CH₂CH₃ A-28H C(═O)—OCH(CH₃)CH₂CH₃ A-29 H C(═O)—OCH₂CH(CH₃)CH₃ A-30 H C(═O)—OC(CH₃)₃A-31 H C(═O)—OCH₂CH₂CH₂CH₂CH₃ A-32 H C(═O)—OCH(CH₃)CH₂CH₂CH₃ A-33 HC(═O)—OCH₂CH(CH₃)CH₂CH₃ A-34 H C(═O)—OCH₂CH₂CH(CH₃)CH₃ A-35 HC(═O)—OCH(CH₂CH₃)CH₂CH₃ A-36 H allyl A-37 H propargyl A-38 H cyclopropylA-39 H cylopentyl A-40 H cyclohexyl A-41 H phenyl A-42 H 2-pyridyl A-43H 3-pyridyl A-44 H 4-pyridyl A-45 H 2-F-phenyl A-46 H 3-F-phenyl A-47 H4-F-phenyl A-48 H 2-Cl-phenyl A-49 H 3-Cl-phenyl A-50 H 4-Cl-phenyl A-51H 2-methyl-phenyl A-52 H 3-methyl-phenyl A-53 H 4-methyl-phenyl A-54 H2-ethyl-phenyl A-55 H 3-ethyl-phenyl A-56 H 4-ethyl-phenyl A-57 H2-isopropyl-phenyl A-58 H 3-isopropyl-phenyl A-59 H 4-isopropyl-phenylA-60 H 2-(2,2,2-trifluoroethyl)-phenyl A-61 H3-(2,2,2-trifluoroethyl)-phenyl A-62 H 4-(2,2,2-trifluoroethyl)-phenylA-63 H 2-trifluoromethyl-phenyl A-64 H 3-trifluoromethyl-phenyl A-65 H4-trifluoromethyl-phenyl A-66 H 2-methoxy-phenyl A-67 H 3-methoxy-phenylA-68 H 4-methoxy-phenyl A-69 H 2-trifluoromethoxy-phenyl A-70 H3-trifluoromethoxy-phenyl A-71 H 4-trifluoromethoxy-phenyl A-72 H2-difluoromethoxy-phenyl A-73 H 3-difluoromethoxy-phenyl A-74 H4-difluoromethoxy-phenyl A-75 H 2-(2,2,2-trifluoroethoxy)-phenyl A-76 H3-(2,2,2-trifluoroethoxy)-phenyl A-77 H 4-(2,2,2-trifluoroethoxy)-phenylA-78 H 2-cyano-phenyl A-79 H 3-cyano-phenyl A-80 H 4-cyano-phenyl A-81 H2,3-difluoro-phenyl A-82 H 2,4-difluoro-phenyl A-83 H2,5-difluoro-phenyl A-84 H 2,6-difluoro-phenyl A-85 H2,3-dichloro-phenyl A-86 H 2,4-dichloro-phenyl A-87 H2,5-dichloro-phenyl A-88 H 2,6-dichloro-phenyl A-89 H 2-F-3-Cl-phenylA-90 H 2-F-4-Cl-phenyl A-91 H 2-F-5-Cl-phenyl A-92 H 2-F-6-Cl-phenylA-93 H 3-F-4-Cl-phenyl A-94 H 3-F-5-Cl-phenyl A-95 H 2-Cl-3-F-phenylA-96 H 2-Cl-4-F-phenyl A-97 H 2-Cl-5-F-phenyl A-98 H 3-Cl-4-F-phenylA-99 H 2-F-3-methyl-phenyl A-100 H 2-F-4-methyl-phenyl A-101 H2-F-5-methyl-phenyl A-102 H 2-F-6-methyl-phenyl A-103 H3-F-4-methyl-phenyl A-104 H 3-F-5-methyl-phenyl A-105 H2-methyl-3-F-phenyl A-106 H 2-methyl-4-F-phenyl A-107 H2-methyl-5-F-phenyl A-108 H 3-methyl-4-F-phenyl A-109 H 2-F-3-CF₃-phenylA-110 H 2-F-4-CF₃-phenyl A-111 H 2-F-5-CF₃-phenyl A-112 H2-F-6-CF₃-phenyl A-113 H 3-F-4-CF₃-phenyl A-114 H 3-F-5-CF₃-phenyl A-115H 2-CF₃-3-F-phenyl A-116 H 2-CF₃-4-F-phenyl A-117 H 2-CF₃-5-F-phenylA-118 H 3-CF₃-4-F-phenyl A-119 H 2-F-3-OMe-phenyl A-120 H2-F-4-OMe-phenyl A-121 H 2-F-5-OMe-phenyl A-122 H 2-F-6-OMe-phenyl A-123H 3-F-4-OMe-phenyl A-124 H 3-F-5-OMe-phenyl A-125 H 2-OMe-3-F-phenylA-126 H 2-OMe-4-F-phenyl A-127 H 2-OMe-5-F-phenyl A-128 H3-OMe-4-F-phenyl A-129 H 2-F-3-OCHF₂-phenyl A-130 H 2-F-4-OCHF₂-phenylA-131 H 2-F-5-OCHF₂-phenyl A-132 H 2-F-6-OCHF₂-phenyl A-133 H3-F-4-OCHF₂-phenyl A-134 H 3-F-5-OCHF₂-phenyl A-135 H 2-OCHF₂-3-F-phenylA-136 H 2-OCHF₂-4-F-phenyl A-137 H 2-OCHF₂-5-F-phenyl A-138 H3-OCHF₂-4-F-phenyl A-139 H 2-F-3-CN-phenyl A-140 H 2-F-4-CN-phenyl A-141H 2-F-5-CN-phenyl A-142 H 2-F-6-CN-phenyl A-143 H 3-F-4-CN-phenyl A-144H 3-F-5-CN-phenyl A-145 H 2-CN-3-F-phenyl A-146 H 2-CN-4-F-phenyl A-147H 2-CN-5-F-phenyl A-148 H 3-CN-4-F-phenyl A-149 H 2-Cl-3-methyl-phenylA-150 H 2-Cl-4-methyl-phenyl A-151 H 2-Cl-5-methyl-phenyl A-152 H2-Cl-6-methyl-phenyl A-153 H 3-Cl-4-methyl-phenyl A-154 H3-Cl-5-methyl-phenyl A-155 H 2-methyl-3-Cl-phenyl A-156 H2-methyl-4-Cl-phenyl A-157 H 2-methyl-5-Cl-phenyl A-158 H3-methyl-4-Cl-phenyl A-159 H 2-Cl-3-CF₃-phenyl A-160 H 2-Cl-4-CF₃-phenylA-161 H 2-Cl-5-CF₃-phenyl A-162 H 2-Cl-6-CF₃-phenyl A-163 H3-Cl-4-CF₃-phenyl A-164 H 3-Cl-5-CF₃-phenyl A-165 H 2-CF₃-3-Cl-phenylA-166 H 2-CF₃-4-Cl-phenyl A-167 H 2-CF₃-5-Cl-phenyl A-168 H3-CF₃-4-Cl-phenyl A-169 H 2-Cl-3-OMe-phenyl A-170 H 2-Cl-4-OMe-phenylA-171 H 2-Cl-5-OMe-phenyl A-172 H 2-Cl-6-OMe-phenyl A-173 H3-Cl-4-OMe-phenyl A-174 H 3-Cl-5-OMe-phenyl A-175 H 2-OMe-3-Cl-phenylA-176 H 2-OMe-4-Cl-phenyl A-177 H 2-OMe-5-Cl-phenyl A-178 H3-OMe-4-Cl-phenyl A-179 H 2-Cl-3-OCHF₂-phenyl A-180 H2-Cl-4-OCHF₂-phenyl A-181 H 2-Cl-5-OCHF₂-phenyl A-182 H2-Cl-6-OCHF₂-phenyl A-183 H 3-Cl-4-OCHF₂-phenyl A-184 H3-Cl-5-OCHF₂-phenyl A-185 H 2-OCHF₂-3-Cl-phenyl A-186 H2-OCHF₂-4-Cl-phenyl A-187 H 2-OCHF₂-5-Cl-phenyl A-188 H3-OCHF₂-4-Cl-phenyl A-189 H 2-Cl-3-CN-phenyl A-190 H 2-Cl-4-CN-phenylA-191 H 2-Cl-5-CN-phenyl A-192 H 2-Cl-6-CN-phenyl A-193 H3-Cl-4-CN-phenyl A-194 H 3-Cl-5-CN-phenyl A-195 H 2-CN-3-Cl-phenyl A-196H 2-CN-4-Cl-phenyl A-197 H 2-CN-5-Cl-phenyl A-198 H 3-CN-4-Cl-phenylA-199 H CH₂-cyclopropyl A-200 H CH₂-cyclopentyl A-201 H CH₂-cyclohexylA-202 H CH₂-(4-quinolinyl) A-203 H CH₂-(2-pyridyl) A-204 HCH₂-(3-pyridyl) A-205 H CH₂-(4-pyridyl) A-206 H CH₂-(2-thienyl) A-207 HCH₂-(3-thienyl) A-208 H CH₂-(N-methyl-3-pyrazolyl) A-209 HCH₂-(N-methyl-4-pyrazolyl) A-210 H CH₂-(1-pyrazolyl) A-211 HCH₂-(2-oxazolyl) A-212 H CH₂-(4-oxazolyl) A-213 H CH₂-(5-oxazolyl) A-214H CH₂-(2-(1,3,4-oxadiazolyl)) A-215 H CH₂-(2-furyl) A-216 HCH₂-(3-furyl) A-217 H 3-hydroxypropyl A-218 HCH₂-(N-methyl-3-pyrrolidinyl) A-219 H 3-dimethylaminopropyl A-220 H2-dimethylaminoethyl A-221 H 3-pyrrolidinyl A-222 H benzyl A-223 H(2-F-phenyl)methyl A-224 H (3-F-phenyl)methyl A-225 H (4-F-phenyl)methylA-226 H (2-Cl-phenyl)methyl A-227 H (3-Cl-phenyl)methyl A-228 H(4-Cl-phenyl)methyl A-229 H (2-methyl-phenyl)methyl A-230 H(3-methyl-phenyl)methyl A-231 H (4-methyl-phenyl)methyl A-232 H(2-methoxy-phenyl)methyl A-233 H (3-methoxy-phenyl)methyl A-234 H(4-methoxy-phenyl)methyl A-235 H (2-cyano-phenyl)methyl A-236 H(3-cyano-phenyl)methyl A-237 H (4-cyano-phenyl)methyl A-238 H(2,3-difluoro-phenyl)methyl A-239 H (2,4-difluoro-phenyl)methyl A-240 H(2,5-difluoro-phenyl)methyl A-241 H (2,6-difluoro-phenyl)methyl A-242 H(2,3-dichloro-phenyl)methyl A-243 H (2,4-dichloro-phenyl)methyl A-244 H(2,5-dichloro-phenyl)methyl A-245 H (2,6-dichloro-phenyl)methyl A-246 R¹and R² together with the nitrogen to which they are bound form aaziridinyl A-247 R¹ and R² together with the nitrogen to which they arebound form a azetidinyl A-248 R¹ and R² together with the nitrogen towhich they are bound form a 1-pyrrolidinyl A-249 R¹ and R² together withthe nitrogen to which they are bound form a 1-piperidinyl A-250 R¹ andR² together with the nitrogen to which they are bound form a1-piperazinyl A-251 R¹ and R² together with the nitrogen to which theyare bound form a 1-methyl-4-piperazinyl A-252 R¹ and R² together withthe nitrogen to which they are bound form a 4-morpholinyl A-253 CH₃ CH₃A-254 CH₃ CH₂CH₃ A-255 CH₃ CH₂CH₂CH₃ A-256 CH₃ CH(CH₃)₂ A-257 CH₃CH₂CH₂CH₂CH₃ A-258 CH₃ CH(CH₃)CH₂CH₃ A-259 CH₃ CH₂CH(CH₃)CH₃ A-260 CH₃C(CH₃)₃ A-261 CH₃ C(═O)—CH₃ A-262 CH₃ C(═O)—CH₂CH₃ A-263 CH₃C(═O)—CH₂CH₂CH₃ A-264 CH₃ C(═O)—CH(CH₃)₂ A-265 CH₃ C(═O)—CH₂CH₂CH₂CH₃A-266 CH₃ C(═O)—CH(CH₃)CH₂CH₃ A-267 CH₃ C(═O)—CH₂CH(CH₃)CH₃ A-268 CH₃C(═O)—C(CH₃)₃ A-269 CH₃ C(═O)—CH₂CH₂CH₂CH₂CH₃ A-270 CH₃C(═O)—CH(CH₃)CH₂CH₂CH₃ A-271 CH₃ C(═O)—CH₂CH(CH₃)CH₂CH₃ A-272 CH₃C(═O)—CH₂CH₂CH(CH₃)CH₃ A-273 CH₃ C(═O)—CH(CH₂CH₃)CH₂CH₃ A-274 CH₃C(═O)—OCH₃ A-275 CH₃ C(═O)—OCH₂CH₃ A-276 CH₃ C(═O)—OCH₂CH₂CH₃ A-277 CH₃C(═O)—OCH(CH₃)₂ A-278 CH₃ C(═O)—OCH₂CH₂CH₂CH₃ A-279 CH₃C(═O)—OCH(CH₃)CH₂CH₃ A-280 CH₃ C(═O)—OCH₂CH(CH₃)CH₃ A-281 CH₃C(═O)—OC(CH₃)₃ A-282 CH₃ C(═O)—OCH₂CH₂CH₂CH₂CH₃ A-283 CH₃C(═O)—OCH(CH₃)CH₂CH₂CH₃ A-284 CH₃ C(═O)—OCH₂CH(CH₃)CH₂CH₃ A-285 CH₃C(═O)—OCH₂CH₂CH(CH₃)CH₃ A-286 CH₃ C(═O)—OCH(CH₂CH₃)CH₂CH₃ A-287 CH₃allyl A-288 CH₃ propargyl A-289 CH₃ cyclopropyl A-290 CH₃ cylopentylA-291 CH₃ cyclohexyl A-292 CH₃ phenyl A-293 CH₃ 2-pyridyl A-294 CH₃3-pyridyl A-295 CH₃ 4-pyridyl A-296 CH₃ 2-F-phenyl A-297 CH₃ 3-F-phenylA-298 CH₃ 4-F-phenyl A-299 CH₃ 2-Cl-phenyl A-300 CH₃ 3-Cl-phenyl A-301CH₃ 4-Cl-phenyl A-302 CH₃ 2-methyl-phenyl A-303 CH₃ 3-methyl-phenylA-304 CH₃ 4-methyl-phenyl A-305 CH₃ 2-ethyl-phenyl A-306 CH₃3-ethyl-phenyl A-307 CH₃ 4-ethyl-phenyl A-308 CH₃ 2-isopropyl-phenylA-309 CH₃ 3-isopropyl-phenyl A-310 CH₃ 4-isopropyl-phenyl A-311 CH₃2-(2,2,2-trifluoroethyl)-phenyl A-312 CH₃3-(2,2,2-trifluoroethyl)-phenyl A-313 CH₃4-(2,2,2-trifluoroethyl)-phenyl A-314 CH₃ 2-trifluoromethyl-phenyl A-315CH₃ 3-trifluoromethyl-phenyl A-316 CH₃ 4-trifluoromethyl-phenyl A-317CH₃ 2-methoxy-phenyl A-318 CH₃ 3-methoxy-phenyl A-319 CH₃4-methoxy-phenyl A-320 CH₃ 2-trifluoromethoxy-phenyl A-321 CH₃3-trifluoromethoxy-phenyl A-322 CH₃ 4-trifluoromethoxy-phenyl A-323 CH₃2-difluoromethoxy-phenyl A-324 CH₃ 3-difluoromethoxy-phenyl A-325 CH₃4-difluoromethoxy-phenyl A-326 CH₃ 2-(2,2,2-trifluoroethoxy)-phenylA-327 CH₃ 3-(2,2,2-trifluoroethoxy)-phenyl A-328 CH₃4-(2,2,2-trifluoroethoxy)-phenyl A-329 CH₃ 2-cyano-phenyl A-330 CH₃3-cyano-phenyl A-331 CH₃ 4-cyano-phenyl A-332 CH₃ 2,3-difluoro-phenylA-333 CH₃ 2,4-difluoro-phenyl A-334 CH₃ 2,5-difluoro-phenyl A-335 CH₃2,6-difluoro-phenyl A-336 CH₃ 2,3-dichloro-phenyl A-337 CH₃2,4-dichloro-phenyl A-338 CH₃ 2,5-dichloro-phenyl A-339 CH₃2,6-dichloro-phenyl A-340 CH₃ 2-F-3-Cl-phenyl A-341 CH₃ 2-F-4-Cl-phenylA-342 CH₃ 2-F-5-Cl-phenyl A-343 CH₃ 2-F-6-Cl-phenyl A-344 CH₃3-F-4-Cl-phenyl A-345 CH₃ 3-F-5-Cl-phenyl A-346 CH₃ 2-Cl-3-F-phenylA-347 CH₃ 2-Cl-4-F-phenyl A-348 CH₃ 2-Cl-5-F-phenyl A-349 CH₃3-Cl-4-F-phenyl A-350 CH₃ 2-F-3-methyl-phenyl A-351 CH₃2-F-4-methyl-phenyl A-352 CH₃ 2-F-5-methyl-phenyl A-353 CH₃2-F-6-methyl-phenyl A-354 CH₃ 3-F-4-methyl-phenyl A-355 CH₃3-F-5-methyl-phenyl A-356 CH₃ 2-methyl-3-F-phenyl A-357 CH₃2-methyl-4-F-phenyl A-358 CH₃ 2-methyl-5-F-phenyl A-359 CH₃3-methyl-4-F-phenyl A-360 CH₃ 2-F-3-CF₃-phenyl A-361 CH₃2-F-4-CF₃-phenyl A-362 CH₃ 2-F-5-CF₃-phenyl A-363 CH₃ 2-F-6-CF₃-phenylA-364 CH₃ 3-F-4-CF₃-phenyl A-365 CH₃ 3-F-5-CF₃-phenyl A-366 CH₃2-CF₃-3-F-phenyl A-367 CH₃ 2-CF₃-4-F-phenyl A-368 CH₃ 2-CF₃-5-F-phenylA-369 CH₃ 3-CF₃-4-F-phenyl A-370 CH₃ 2-F-3-OMe-phenyl A-371 CH₃2-F-4-OMe-phenyl A-372 CH₃ 2-F-5-OMe-phenyl A-373 CH₃ 2-F-6-OMe-phenylA-374 CH₃ 3-F-4-OMe-phenyl A-375 CH₃ 3-F-5-OMe-phenyl A-376 CH₃2-OMe-3-F-phenyl A-377 CH₃ 2-OMe-4-F-phenyl A-378 CH₃ 2-OMe-5-F-phenylA-379 CH₃ 3-OMe-4-F-phenyl A-380 CH₃ 2-F-3-OCHF₂-phenyl A-381 CH₃2-F-4-OCHF₂-phenyl A-382 CH₃ 2-F-5-OCHF₂-phenyl A-383 CH₃2-F-6-OCHF₂-phenyl A-384 CH₃ 3-F-4-OCHF₂-phenyl A-385 CH₃3-F-5-OCHF₂-phenyl A-386 CH₃ 2-OCHF₂-3-F-phenyl A-387 CH₃2-OCHF₂-4-F-phenyl A-388 CH₃ 2-OCHF₂-5-F-phenyl A-389 CH₃3-OCHF₂-4-F-phenyl A-390 CH₃ 2-F-3-CN-phenyl A-391 CH₃ 2-F-4-CN-phenylA-392 CH₃ 2-F-5-CN-phenyl A-393 CH₃ 2-F-6-CN-phenyl A-394 CH₃3-F-4-CN-phenyl A-395 CH₃ 3-F-5-CN-phenyl A-396 CH₃ 2-CN-3-F-phenylA-397 CH₃ 2-CN-4-F-phenyl A-398 CH₃ 2-CN-5-F-phenyl A-399 CH₃3-CN-4-F-phenyl A-400 CH₃ 2-Cl-3-methyl-phenyl A-401 CH₃2-Cl-4-methyl-phenyl A-402 CH₃ 2-Cl-5-methyl-phenyl A-403 CH₃2-Cl-6-methyl-phenyl A-404 CH₃ 3-Cl-4-methyl-phenyl A-405 CH₃3-Cl-5-methyl-phenyl A-406 CH₃ 2-methyl-3-Cl-phenyl A-407 CH₃2-methyl-4-Cl-phenyl A-408 CH₃ 2-methyl-5-Cl-phenyl A-409 CH₃3-methyl-4-Cl-phenyl A-410 CH₃ 2-Cl-3-CF₃-phenyl A-411 CH₃2-Cl-4-CF₃-phenyl A-412 CH₃ 2-Cl-5-CF₃-phenyl A-413 CH₃2-Cl-6-CF₃-phenyl A-414 CH₃ 3-Cl-4-CF₃-phenyl A-415 CH₃3-Cl-5-CF₃-phenyl A-416 CH₃ 2-CF₃-3-Cl-phenyl A-417 CH₃2-CF₃-4-Cl-phenyl A-418 CH₃ 2-CF₃-5-Cl-phenyl A-419 CH₃3-CF₃-4-Cl-phenyl A-420 CH₃ 2-Cl-3-OMe-phenyl A-421 CH₃2-Cl-4-OMe-phenyl A-422 CH₃ 2-Cl-5-OMe-phenyl A-423 CH₃2-Cl-6-OMe-phenyl A-424 CH₃ 3-Cl-4-OMe-phenyl A-425 CH₃3-Cl-5-OMe-phenyl A-426 CH₃ 2-OMe-3-Cl-phenyl A-427 CH₃2-OMe-4-Cl-phenyl A-428 CH₃ 2-OMe-5-Cl-phenyl A-429 CH₃3-OMe-4-Cl-phenyl A-430 CH₃ 2-Cl-3-OCHF₂-phenyl A-431 CH₃2-Cl-4-OCHF₂-phenyl A-432 CH₃ 2-Cl-5-OCHF₂-phenyl A-433 CH₃2-Cl-6-OCHF₂-phenyl A-434 CH₃ 3-Cl-4-OCHF₂-phenyl A-435 CH₃3-Cl-5-OCHF₂-phenyl A-436 CH₃ 2-OCHF₂-3-Cl-phenyl A-437 CH₃2-OCHF₂-4-Cl-phenyl A-438 CH₃ 2-OCHF₂-5-Cl-phenyl A-439 CH₃3-OCHF₂-4-Cl-phenyl A-440 CH₃ 2-Cl-3-CN-phenyl A-441 CH₃2-Cl-4-CN-phenyl A-442 CH₃ 2-Cl-5-CN-phenyl A-443 CH₃ 2-Cl-6-CN-phenylA-444 CH₃ 3-Cl-4-CN-phenyl A-445 CH₃ 3-Cl-5-CN-phenyl A-446 CH₃2-CN-3-Cl-phenyl A-447 CH₃ 2-CN-4-Cl-phenyl A-448 CH₃ 2-CN-5-Cl-phenylA-449 CH₃ 3-CN-4-Cl-phenyl A-450 CH₃ CH₂-cyclopropyl A-451 CH₃CH₂-cyclopentyl A-452 CH₃ CH₂-cyclohexyl A-453 CH₃ CH₂-(4-quinolinyl)A-454 CH₃ CH₂-(2-pyridyl) A-455 CH₃ CH₂-(3-pyridyl) A-456 CH₃CH₂-(4-pyridyl) A-457 CH₃ CH₂-(2-thienyl) A-458 CH₃ CH₂-(3-thienyl)A-459 CH₃ CH₂-(N-methyl-3-pyrazolyl) A-460 CH₃CH₂-(N-methyl-4-pyrazolyl) A-461 CH₃ CH₂-(1-pyrazolyl) A-462 CH₃CH₂-(2-oxazolyl) A-463 CH₃ CH₂-(4-oxazolyl) A-464 CH₃ CH₂-(5-oxazolyl)A-465 CH₃ CH₂-(2-(1,3,4-oxadiazolyl)) A-466 CH₃ CH₂-(2-furyl) A-467 CH₃CH₂-(3-furyl) A-468 CH₃ 3-hydroxypropyl A-469 CH₃CH₂-(N-methyl-3-pyrrolidinyl) A-470 CH₃ 3-dimethylaminopropyl A-471 CH₃2-dimethylaminoethyl A-472 CH₃ 3-pyrrolidinyl A-473 CH₃ benzyl A-474 CH₃(2-F-phenyl)methyl A-475 CH₃ (3-F-phenyl)methyl A-476 CH₃(4-F-phenyl)methyl A-477 CH₃ (2-Cl-phenyl)methyl A-478 CH₃(3-Cl-phenyl)methyl A-479 CH₃ (4-Cl-phenyl)methyl A-480 CH₃(2-methyl-phenyl)methyl A-481 CH₃ (3-methyl-phenyl)methyl A-482 CH₃(4-methyl-phenyl)methyl A-483 CH₃ (2-methoxy-phenyl)methyl A-484 CH₃(3-methoxy-phenyl)methyl A-485 CH₃ (4-methoxy-phenyl)methyl A-486 CH₃(2-cyano-phenyl)methyl A-487 CH₃ (3-cyano-phenyl)methyl A-488 CH₃(4-cyano-phenyl)methyl A-489 CH₃ (2,3-difluoro-phenyl)methyl A-490 CH₃(2,4-difluoro-phenyl)methyl A-491 CH₃ (2,5-difluoro-phenyl)methyl A-492CH₃ (2,6-difluoro-phenyl)methyl A-493 CH₃ (2,3-dichloro-phenyl)methylA-494 CH₃ (2,4-dichloro-phenyl)methyl A-495 CH₃(2,5-dichloro-phenyl)methyl A-496 CH₃ (2,6-dichloro-phenyl)methyl A-497ethyl H A-498 ethyl CH₃ A-499 ethyl CH₂CH₃ A-500 ethyl CH₂CH₂CH₃ A-501ethyl CH(CH₃)₂ A-502 ethyl CH₂CH₂CH₂CH₃ A-503 ethyl CH(CH₃)CH₂CH₃ A-504ethyl CH₂CH(CH₃)CH₃ A-505 ethyl C(CH₃)₃ A-506 ethyl C(═O)—CH₃ A-507ethyl C(═O)—CH₂CH₃ A-508 ethyl C(═O)—CH₂CH₂CH₃ A-509 ethylC(═O)—CH(CH₃)₂ A-510 ethyl C(═O)—CH₂CH₂CH₂CH₃ A-511 ethylC(═O)—CH(CH₃)CH₂CH₃ A-512 ethyl C(═O)—CH₂CH(CH₃)CH₃ A-513 ethylC(═O)—C(CH₃)₃ A-514 ethyl C(═O)—CH₂CH₂CH₂CH₂CH₃ A-515 ethylC(═O)—CH(CH₃)CH₂CH₂CH₃ A-516 ethyl C(═O)—CH₂CH(CH₃)CH₂CH₃ A-517 ethylC(═O)—CH₂CH₂CH(CH₃)CH₃ A-518 ethyl C(═O)—CH(CH₂CH₃)CH₂CH₃ A-519 ethylC(═O)—OCH₃ A-520 ethyl C(═O)—OCH₂CH₃ A-521 ethyl C(═O)—OCH₂CH₂CH₃ A-522ethyl C(═O)—OCH(CH₃)₂ A-523 ethyl C(═O)—OCH₂CH₂CH₂CH₃ A-524 ethylC(═O)—OCH(CH₃)CH₂CH₃ A-525 ethyl C(═O)—OCH₂CH(CH₃)CH₃ A-526 ethylC(═O)—OC(CH₃)₃ A-527 ethyl C(═O)—OCH₂CH₂CH₂CH₂CH₃ A-528 ethylC(═O)—OCH(CH₃)CH₂CH₂CH₃ A-529 ethyl C(═O)—OCH₂CH(CH₃)CH₂CH₃ A-530 ethylC(═O)—OCH₂CH₂CH(CH₃)CH₃ A-531 ethyl C(═O)—OCH(CH₂CH₃)CH₂CH₃ A-532 ethylallyl A-533 ethyl propargyl A-534 ethyl cyclopropyl A-535 ethylcylopentyl A-536 ethyl cyclohexyl A-537 ethyl phenyl A-538 ethyl2-pyridyl A-539 ethyl 3-pyridyl A-540 ethyl 4-pyridyl A-541 ethyl2-F-phenyl A-542 ethyl 3-F-phenyl A-543 ethyl 4-F-phenyl A-544 ethyl2-Cl-phenyl A-545 ethyl 3-Cl-phenyl A-546 ethyl 4-Cl-phenyl A-547 ethyl2-methyl-phenyl A-548 ethyl 3-methyl-phenyl A-549 ethyl 4-methyl-phenylA-550 i-propyl H A-551 i-propyl CH₃ A-552 i-propyl CH₂CH₃ A-553 i-propylCH₂CH₂CH₃ A-554 i-propyl CH(CH₃)₂ A-555 i-propyl CH₂CH₂CH₂CH₃ A-556i-propyl CH(CH₃)CH₂CH₃ A-557 i-propyl CH₂CH(CH₃)CH₃ A-558 i-propylC(CH₃)₃ A-559 i-propyl C(═O)—CH₃ A-560 i-propyl C(═O)—CH₂CH₃ A-561i-propyl C(═O)—CH₂CH₂CH₃ A-562 i-propyl C(═O)—CH(CH₃)₂ A-563 i-propylC(═O)—CH₂CH₂CH₂CH₃ A-564 i-propyl C(═O)—CH(CH₃)CH₂CH₃ A-565 i-propylC(═O)—CH₂CH(CH₃)CH₃ A-566 i-propyl C(═O)—C(CH₃)₃ A-567 i-propylC(═O)—CH₂CH₂CH₂CH₂CH₃ A-568 i-propyl C(═O)—CH(CH₃)CH₂CH₂CH₃ A-569i-propyl C(═O)—CH₂CH(CH₃)CH₂CH₃ A-570 i-propyl C(═O)—CH₂CH₂CH(CH₃)CH₃A-571 i-propyl C(═O)—CH(CH₂CH₃)CH₂CH₃ A-572 i-propyl C(═O)—OCH₃ A-573i-propyl C(═O)—OCH₂CH₃ A-574 i-propyl C(═O)—OCH₂CH₂CH₃ A-575 i-propylC(═O)—OCH(CH₃)₂ A-576 i-propyl C(═O)—OCH₂CH₂CH₂CH₃ A-577 i-propylC(═O)—OCH(CH₃)CH₂CH₃ A-578 i-propyl C(═O)—OCH₂CH(CH₃)CH₃ A-579 i-propylC(═O)—OC(CH₃)₃ A-580 i-propyl C(═O)—OCH₂CH₂CH₂CH₂CH₃ A-581 i-propylC(═O)—OCH(CH₃)CH₂CH₂CH₃ A-582 i-propyl C(═O)—OCH₂CH(CH₃)CH₂CH₃ A-583i-propyl C(═O)—OCH₂CH₂CH(CH₃)CH₃ A-584 i-propyl C(═O)—OCH(CH₂CH₃)CH₂CH₃A-585 i-propyl allyl A-586 i-propyl propargyl A-587 i-propyl cyclopropylA-588 i-propyl cylopentyl A-589 i-propyl cyclohexyl A-590 i-propylphenyl A-591 i-propyl 2-pyridyl A-592 i-propyl 3-pyridyl A-593 i-propyl4-pyridyl A-594 i-propyl 2-F-phenyl A-595 i-propyl 3-F-phenyl A-596i-propyl 4-F-phenyl A-597 i-propyl 2-Cl-phenyl A-598 i-propyl3-Cl-phenyl A-599 i-propyl 4-Cl-phenyl A-600 i-propyl 2-methyl-phenylA-601 i-propyl 3-methyl-phenyl A-602 i-propyl 4-methyl-phenyl A-603n-propyl H A-604 n-propyl CH₃ A-605 n-propyl CH₂CH₃ A-606 n-propylCH₂CH₂CH₃ A-607 n-propyl CH(CH₃)₂ A-608 n-propyl CH₂CH₂CH₂CH₃ A-609n-propyl CH(CH₃)CH₂CH₃ A-610 n-propyl CH₂CH(CH₃)CH₃ A-611 n-propylC(CH₃)₃ A-612 n-propyl C(═O)—CH₃ A-613 n-propyl C(═O)—CH₂CH₃ A-614n-propyl C(═O)—CH₂CH₂CH₃ A-615 n-propyl C(═O)—CH(CH₃)₂ A-616 n-propylC(═O)—CH₂CH₂CH₂CH₃ A-617 n-propyl C(═O)—CH(CH₃)CH₂CH₃ A-618 n-propylC(═O)—CH₂CH(CH₃)CH₃ A-619 n-propyl C(═O)—C(CH₃)₃ A-620 n-propylC(═O)—CH₂CH₂CH₂CH₂CH₃ A-621 n-propyl C(═O)—CH(CH₃)CH₂CH₂CH₃ A-622n-propyl C(═O)—CH₂CH(CH₃)CH₂CH₃ A-623 n-propyl C(═O)—CH₂CH₂CH(CH₃)CH₃A-624 n-propyl C(═O)—CH(CH₂CH₃)CH₂CH₃ A-625 n-propyl C(═O)—OCH₃ A-626n-propyl C(═O)—OCH₂CH₃ A-627 n-propyl C(═O)—OCH₂CH₂CH₃ A-628 n-propylC(═O)—OCH(CH₃)₂ A-629 n-propyl C(═O)—OCH₂CH₂CH₂CH₃ A-630 n-propylC(═O)—OCH(CH₃)CH₂CH₃ A-631 n-propyl C(═O)—OCH₂CH(CH₃)CH₃ A-632 n-propylC(═O)—OC(CH₃)₃ A-633 n-propyl C(═O)—OCH₂CH₂CH₂CH₂CH₃ A-634 n-propylC(═O)—OCH(CH₃)CH₂CH₂CH₃ A-635 n-propyl C(═O)—OCH₂CH(CH₃)CH₂CH₃ A-636n-propyl C(═O)—OCH₂CH₂CH(CH₃)CH₃ A-637 n-propyl C(═O)—OCH(CH₂CH₃)CH₂CH₃A-638 n-propyl allyl A-639 n-propyl propargyl A-640 n-propyl cyclopropylA-641 n-propyl cylopentyl A-642 n-propyl cyclohexyl A-643 n-propylphenyl A-644 n-propyl 2-pyridyl A-645 n-propyl 3-pyridyl A-646 n-propyl4-pyridyl A-647 n-propyl 2-F-phenyl A-648 n-propyl 3-F-phenyl A-649n-propyl 4-F-phenyl A-650 n-propyl 2-Cl-phenyl A-651 n-propyl3-Cl-phenyl A-652 n-propyl 4-Cl-phenyl A-653 n-propyl 2-methyl-phenylA-654 n-propyl 3-methyl-phenyl A-655 n-propyl 4-methyl-phenyl A-656allyl H A-657 allyl CH₃ A-658 allyl CH₂CH₃ A-659 allyl CH₂CH₂CH₃ A-660allyl CH(CH₃)₂ A-661 allyl CH₂CH₂CH₂CH₃ A-662 allyl CH(CH₃)CH₂CH₃ A-663allyl CH₂CH(CH₃)CH₃ A-664 allyl C(CH₃)₃ A-665 allyl C(═O)—CH₃ A-666allyl C(═O)—CH₂CH₃ A-667 allyl C(═O)—CH₂CH₂CH₃ A-668 allylC(═O)—CH(CH₃)₂ A-669 allyl C(═O)—CH₂CH₂CH₂CH₃ A-670 allylC(═O)—CH(CH₃)CH₂CH₃ A-671 allyl C(═O)—CH₂CH(CH₃)CH₃ A-672 allylC(═O)—C(CH₃)₃ A-673 allyl C(═O)—CH₂CH₂CH₂CH₂CH₃ A-674 allylC(═O)—CH(CH₃)CH₂CH₂CH₃ A-675 allyl C(═O)—CH₂CH(CH₃)CH₂CH₃ A-676 allylC(═O)—CH₂CH₂CH(CH₃)CH₃ A-677 allyl C(═O)—CH(CH₂CH₃)CH₂CH₃ A-678 allylC(═O)—OCH₃ A-679 allyl C(═O)—OCH₂CH₃ A-680 allyl C(═O)—OCH₂CH₂CH₃ A-681allyl C(═O)—OCH(CH₃)₂ A-682 allyl C(═O)—OCH₂CH₂CH₂CH₃ A-683 allylC(═O)—OCH(CH₃)CH₂CH₃ A-684 allyl C(═O)—OCH₂CH(CH₃)CH₃ A-685 allylC(═O)—OC(CH₃)₃ A-686 allyl C(═O)—OCH₂CH₂CH₂CH₂CH₃ A-687 allylC(═O)—OCH(CH₃)CH₂CH₂CH₃ A-688 allyl C(═O)—OCH₂CH(CH₃)CH₂CH₃ A-689 allylC(═O)—OCH₂CH₂CH(CH₃)CH₃ A-690 allyl C(═O)—OCH(CH₂CH₃)CH₂CH₃ A-691 allylallyl A-692 allyl propargyl A-693 allyl cyclopropyl A-694 allylcylopentyl A-695 allyl cyclohexyl A-696 allyl phenyl A-697 allyl2-pyridyl A-698 allyl 3-pyridyl A-699 allyl 4-pyridyl A-700 allyl2-F-phenyl A-701 allyl 3-F-phenyl A-702 allyl 4-F-phenyl A-703 allyl2-Cl-phenyl A-704 allyl 3-Cl-phenyl A-705 allyl 4-Cl-phenyl A-706 allyl2-methyl-phenyl A-707 allyl 3-methyl-phenyl A-708 allyl 4-methyl-phenylA-709 tert-butyl H A-710 tert-butyl CH₃ A-711 tert-butyl CH₂CH₃ A-712tert-butyl CH₂CH₂CH₃ A-713 tert-butyl CH(CH₃)₂ A-714 tert-butylCH₂CH₂CH₂CH₃ A-715 tert-butyl CH(CH₃)CH₂CH₃ A-716 tert-butylCH₂CH(CH₃)CH₃ A-717 tert-butyl C(CH₃)₃ A-718 tert-butyl C(═O)—CH₃ A-719tert-butyl C(═O)—CH₂CH₃ A-720 tert-butyl C(═O)—CH₂CH₂CH₃ A-721tert-butyl C(═O)—CH(CH₃)₂ A-722 tert-butyl C(═O)—CH₂CH₂CH₂CH₃ A-723tert-butyl C(═O)—CH(CH₃)CH₂CH₃ A-724 tert-butyl C(═O)—CH₂CH(CH₃)CH₃A-725 tert-butyl C(═O)—C(CH₃)₃ A-726 tert-butyl C(═O)—CH₂CH₂CH₂CH₂CH₃A-727 tert-butyl C(═O)—CH(CH₃)CH₂CH₂CH₃ A-728 tert-butylC(═O)—CH₂CH(CH₃)CH₂CH₃ A-729 tert-butyl C(═O)—CH₂CH₂CH(CH₃)CH₃ A-730tert-butyl C(═O)—CH(CH₂CH₃)CH₂CH₃ A-731 tert-butyl C(═O)—OCH₃ A-732tert-butyl C(═O)—OCH₂CH₃ A-733 tert-butyl C(═O)—OCH₂CH₂CH₃ A-734tert-butyl C(═O)—OCH(CH₃)₂ A-735 tert-butyl C(═O)—OCH₂CH₂CH₂CH₃ A-736tert-butyl C(═O)—OCH(CH₃)CH₂CH₃ A-737 tert-butyl C(═O)—OCH₂CH(CH₃)CH₃A-738 tert-butyl C(═O)—OC(CH₃)₃ A-739 tert-butyl C(═O)—OCH₂CH₂CH₂CH₂CH₃A-740 tert-butyl C(═O)—OCH(CH₃)CH₂CH₂CH₃ A-741 tert-butylC(═O)—OCH₂CH(CH₃)CH₂CH₃ A-742 tert-butyl C(═O)—OCH₂CH₂CH(CH₃)CH₃ A-743tert-butyl C(═O)—OCH(CH₂CH₃)CH₂CH₃ A-744 tert-butyl allyl A-745tert-butyl propargyl A-746 tert-butyl cyclopropyl A-747 tert-butylcylopentyl A-748 tert-butyl cyclohexyl A-749 tert-butyl phenyl A-750tert-butyl 2-pyridyl A-751 tert-butyl 3-pyridyl A-752 tert-butyl4-pyridyl A-753 tert-butyl 2-F-phenyl A-754 tert-butyl 3-F-phenyl A-755tert-butyl 4-F-phenyl A-756 tert-butyl 2-Cl-phenyl A-757 tert-butyl3-Cl-phenyl A-758 tert-butyl 4-Cl-phenyl A-759 tert-butyl2-methyl-phenyl A-760 tert-butyl 3-methyl-phenyl A-761 tert-butyl4-methyl-phenyl A-762 phenyl H A-763 phenyl CH₃ A-764 phenyl CH₂CH₃A-765 phenyl CH₂CH₂CH₃ A-766 phenyl CH(CH₃)₂ A-767 phenyl CH₂CH₂CH₂CH₃A-768 phenyl CH(CH₃)CH₂CH₃ A-769 phenyl CH₂CH(CH₃)CH₃ A-770 phenylC(CH₃)₃ A-771 phenyl C(═O)—CH₃ A-772 phenyl C(═O)—CH₂CH₃ A-773 phenylC(═O)—CH₂CH₂CH₃ A-774 phenyl C(═O)—CH(CH₃)₂ A-775 phenylC(═O)—CH₂CH₂CH₂CH₃ A-776 phenyl C(═O)—CH(CH₃)CH₂CH₃ A-777 phenylC(═O)—CH₂CH(CH₃)CH₃ A-778 phenyl C(═O)—C(CH₃)₃ A-779 phenylC(═O)—CH₂CH₂CH₂CH₂CH₃ A-780 phenyl C(═O)—CH(CH₃)CH₂CH₂CH₃ A-781 phenylC(═O)—CH₂CH(CH₃)CH₂CH₃ A-782 phenyl C(═O)—CH₂CH₂CH(CH₃)CH₃ A-783 phenylC(═O)—CH(CH₂CH₃)CH₂CH₃ A-784 phenyl C(═O)—OCH₃ A-785 phenylC(═O)—OCH₂CH₃ A-786 phenyl C(═O)—OCH₂CH₂CH₃ A-787 phenyl C(═O)—OCH(CH₃)₂A-788 phenyl C(═O)—OCH₂CH₂CH₂CH₃ A-789 phenyl C(═O)—OCH(CH₃)CH₂CH₃ A-790phenyl C(═O)—OCH₂CH(CH₃)CH₃ A-791 phenyl C(═O)—OC(CH₃)₃ A-792 phenylC(═O)—OCH₂CH₂CH₂CH₂CH₃ A-793 phenyl C(═O)—OCH(CH₃)CH₂CH₂CH₃ A-794 phenylC(═O)—OCH₂CH(CH₃)CH₂CH₃ A-795 phenyl C(═O)—OCH₂CH₂CH(CH₃)CH₃ A-796phenyl C(═O)—OCH(CH₂CH₃)CH₂CH₃ A-797 phenyl allyl A-798 phenyl propargylA-799 phenyl cyclopropyl A-800 phenyl cylopentyl A-801 phenyl cyclohexylA-802 phenyl phenyl A-803 phenyl 2-pyridyl A-804 phenyl 3-pyridyl A-805phenyl 4-pyridyl A-806 phenyl 2-F-phenyl A-807 phenyl 3-F-phenyl A-808phenyl 4-F-phenyl A-809 phenyl 2-Cl-phenyl A-810 phenyl 3-Cl-phenylA-811 phenyl 4-Cl-phenyl A-812 phenyl 2-methyl-phenyl A-813 phenyl3-methyl-phenyl A-814 phenyl 4-methyl-phenyl A-815 CF₃ H A-816 CF₃ CH₃A-817 CF₃ CH₂CH₃ A-818 CF₃ CH₂CH₂CH₃ A-819 CF₃ CH(CH₃)₂ A-820 CF₃CH₂CH₂CH₂CH₃ A-821 CF₃ CH(CH₃)CH₂CH₃ A-822 CF₃ CH₂CH(CH₃)CH₃ A-823 CF₃C(CH₃)₃ A-824 CF₃ C(═O)—CH₃ A-825 CF₃ C(═O)—CH₂CH₃ A-826 CF₃C(═O)—CH₂CH₂CH₃ A-827 CF₃ C(═O)—CH(CH₃)₂ A-828 CF₃ C(═O)—CH₂CH₂CH₂CH₃A-829 CF₃ C(═O)—CH(CH₃)CH₂CH₃ A-830 CF₃ C(═O)—CH₂CH(CH₃)CH₃ A-831 CF₃C(═O)—C(CH₃)₃ A-832 CF₃ C(═O)—CH₂CH₂CH₂CH₂CH₃ A-833 CF₃C(═O)—CH(CH₃)CH₂CH₂CH₃ A-834 CF₃ C(═O)—CH₂CH(CH₃)CH₂CH₃ A-835 CF₃C(═O)—CH₂CH₂CH(CH₃)CH₃ A-836 CF₃ C(═O)—CH(CH₂CH₃)CH₂CH₃ A-837 CF₃C(═O)—OCH₃ A-838 CF₃ C(═O)—OCH₂CH₃ A-839 CF₃ C(═O)—OCH₂CH₂CH₃ A-840 CF₃C(═O)—OCH(CH₃)₂ A-841 CF₃ C(═O)—OCH₂CH₂CH₂CH₃ A-842 CF₃C(═O)—OCH(CH₃)CH₂CH₃ A-843 CF₃ C(═O)—OCH₂CH(CH₃)CH₃ A-844 CF₃C(═O)—OC(CH₃)₃ A-845 CF₃ C(═O)—OCH₂CH₂CH₂CH₂CH₃ A-846 CF₃C(═O)—OCH(CH₃)CH₂CH₂CH₃ A-847 CF₃ C(═O)—OCH₂CH(CH₃)CH₂CH₃ A-848 CF₃C(═O)—OCH₂CH₂CH(CH₃)CH₃ A-849 CF₃ C(═O)—OCH(CH₂CH₃)CH₂CH₃ A-850 CF₃allyl A-851 CF₃ propargyl A-852 CF₃ cyclopropyl A-853 CF₃ cylopentylA-854 CF₃ cyclohexyl A-855 CF₃ phenyl A-856 CF₃ 2-pyridyl A-857 CF₃3-pyridyl A-858 CF₃ 4-pyridyl A-859 CF₃ 2-F-phenyl A-860 CF₃ 3-F-phenylA-861 CF₃ 4-F-phenyl A-862 CF₃ 2-Cl-phenyl A-863 CF₃ 3-Cl-phenyl A-864CF₃ 4-Cl-phenyl A-865 CF₃ 2-methyl-phenyl A-866 CF₃ 3-methyl-phenylA-867 CF₃ 4-methyl-phenyl A-868 CH₂CF₃ H A-869 CH₂CF₃ CH₃ A-870 CH₂CF₃CH₂CH₃ A-871 CH₂CF₃ CH₂CH₂CH₃ A-872 CH₂CF₃ CH(CH₃)₂ A-873 CH₂CF₃CH₂CH₂CH₂CH₃ A-874 CH₂CF₃ CH(CH₃)CH₂CH₃ A-875 CH₂CF₃ CH₂CH(CH₃)CH₃ A-876CH₂CF₃ C(CH₃)₃ A-877 CH₂CF₃ C(═O)—CH₃ A-878 CH₂CF₃ C(═O)—CH₂CH₃ A-879CH₂CF₃ C(═O)—CH₂CH₂CH₃ A-880 CH₂CF₃ C(═O)—CH(CH₃)₂ A-881 CH₂CF₃C(═O)—CH₂CH₂CH₂CH₃ A-882 CH₂CF₃ C(═O)—CH(CH₃)CH₂CH₃ A-883 CH₂CF₃C(═O)—CH₂CH(CH₃)CH₃ A-884 CH₂CF₃ C(═O)—C(CH₃)₃ A-885 CH₂CF₃C(═O)—CH₂CH₂CH₂CH₂CH₃ A-886 CH₂CF₃ C(═O)—CH(CH₃)CH₂CH₂CH₃ A-887 CH₂CF₃C(═O)—CH₂CH(CH₃)CH₂CH₃ A-888 CH₂CF₃ C(═O)—CH₂CH₂CH(CH₃)CH₃ A-889 CH₂CF₃C(═O)—CH(CH₂CH₃)CH₂CH₃ A-890 CH₂CF₃ C(═O)—OCH₃ A-891 CH₂CF₃C(═O)—OCH₂CH₃ A-892 CH₂CF₃ C(═O)—OCH₂CH₂CH₃ A-893 CH₂CF₃ C(═O)—OCH(CH₃)₂A-894 CH₂CF₃ C(═O)—OCH₂CH₂CH₂CH₃ A-895 CH₂CF₃ C(═O)—OCH(CH₃)CH₂CH₃ A-896CH₂CF₃ C(═O)—OCH₂CH(CH₃)CH₃ A-897 CH₂CF₃ C(═O)—OC(CH₃)₃ A-898 CH₂CF₃C(═O)—OCH₂CH₂CH₂CH₂CH₃ A-899 CH₂CF₃ C(═O)—OCH(CH₃)CH₂CH₂CH₃ A-900 CH₂CF₃C(═O)—OCH₂CH(CH₃)CH₂CH₃ A-901 CH₂CF₃ C(═O)—OCH₂CH₂CH(CH₃)CH₃ A-902CH₂CF₃ C(═O)—OCH(CH₂CH₃)CH₂CH₃ A-903 CH₂CF₃ allyl A-904 CH₂CF₃ propargylA-905 CH₂CF₃ cyclopropyl A-906 CH₂CF₃ cylopentyl A-907 CH₂CF₃ cyclohexylA-908 CH₂CF₃ phenyl A-909 CH₂CF₃ 2-pyridyl A-910 CH₂CF₃ 3-pyridyl A-911CH₂CF₃ 4-pyridyl A-912 CH₂CF₃ 2-F-phenyl A-913 CH₂CF₃ 3-F-phenyl A-914CH₂CF₃ 4-F-phenyl A-915 CH₂CF₃ 2-Cl-phenyl A-916 CH₂CF₃ 3-Cl-phenylA-917 CH₂CF₃ 4-Cl-phenyl A-918 CH₂CF₃ 2-methyl-phenyl A-919 CH₂CF₃3-methyl-phenyl A-920 CH₂CF₃ 4-methyl-phenyl A-921 cyclopropyl H A-922cyclopropyl CH₃ A-923 cyclopropyl CH₂CH₃ A-924 cyclopropyl CH₂CH₂CH₃A-925 cyclopropyl CH(CH₃)₂ A-926 cyclopropyl CH₂CH₂CH₂CH₃ A-927cyclopropyl CH(CH₃)CH₂CH₃ A-928 cyclopropyl CH₂CH(CH₃)CH₃ A-929cyclopropyl C(CH₃)₃ A-930 cyclopropyl C(═O)—CH₃ A-931 cyclopropylC(═O)—CH₂CH₃ A-932 cyclopropyl C(═O)—CH₂CH₂CH₃ A-933 cyclopropylC(═O)—CH(CH₃)₂ A-934 cyclopropyl C(═O)—CH₂CH₂CH₂CH₃ A-935 cyclopropylC(═O)—CH(CH₃)CH₂CH₃ A-936 cyclopropyl C(═O)—CH₂CH(CH₃)CH₃ A-937cyclopropyl C(═O)—C(CH₃)₃ A-938 cyclopropyl C(═O)—CH₂CH₂CH₂CH₂CH₃ A-939cyclopropyl C(═O)—CH(CH₃)CH₂CH₂CH₃ A-940 cyclopropylC(═O)—CH₂CH(CH₃)CH₂CH₃ A-941 cyclopropyl C(═O)—CH₂CH₂CH(CH₃)CH₃ A-942cyclopropyl C(═O)—CH(CH₂CH₃)CH₂CH₃ A-943 cyclopropyl C(═O)—OCH₃ A-944cyclopropyl C(═O)—OCH₂CH₃ A-945 cyclopropyl C(═O)—OCH₂CH₂CH₃ A-946cyclopropyl C(═O)—OCH(CH₃)₂ A-947 cyclopropyl C(═O)—OCH₂CH₂CH₂CH₃ A-948cyclopropyl C(═O)—OCH(CH₃)CH₂CH₃ A-949 cyclopropyl C(═O)—OCH₂CH(CH₃)CH₃A-950 cyclopropyl C(═O)—OC(CH₃)₃ A-951 cyclopropylC(═O)—OCH₂CH₂CH₂CH₂CH₃ A-952 cyclopropyl C(═O)—OCH(CH₃)CH₂CH₂CH₃ A-953cyclopropyl C(═O)—OCH₂CH(CH₃)CH₂CH₃ A-954 cyclopropylC(═O)—OCH₂CH₂CH(CH₃)CH₃ A-955 cyclopropyl C(═O)—OCH(CH₂CH₃)CH₂CH₃ A-956cyclopropyl allyl A-957 cyclopropyl propargyl A-958 cyclopropylcyclopropyl A-959 cyclopropyl cylopentyl A-960 cyclopropyl cyclohexylA-961 cyclopropyl phenyl A-962 cyclopropyl 2-pyridyl A-963 cyclopropyl3-pyridyl A-964 cyclopropyl 4-pyridyl A-965 cyclopropyl 2-F-phenyl A-966cyclopropyl 3-F-phenyl A-967 cyclopropyl 4-F-phenyl A-968 cyclopropyl2-Cl-phenyl A-969 cyclopropyl 3-Cl-phenyl A-970 cyclopropyl 4-Cl-phenylA-971 cyclopropyl 2-methyl-phenyl A-972 cyclopropyl 3-methyl-phenylA-973 cyclopropyl 4-methyl-phenyl

The compounds of the formula I can be prepared according to methods orin analogy to methods that are described in the prior art. The synthesistakes advantage of starting materials that are commercially available ormay be prepared according to conventional procedures starting fromreadily available compounds. For example, compounds of the formula I canbe prepared by reacting amidines of type II with trifluoroaceticanhydride in an organic solvent, preferably an ethereal solvent attemperatures between 0° C. and 100° C., preferably at room temperature,as previously described in WO2013/008162.

A skilled person will recognize that compounds of type II can beaccessed by treating nitriles of type III with hydroxylamine (or its HClsalt) in an organic solvent and in the presence of a base (forprecedents see for example WO2009/074950, WO2006/013104, EP1932843).

Compounds III can be prepared by reacting carbonyl compound of type IVwith the respective amine in an organic solvent and in the presence of abase, followed by subsequent treatment of the intermediary iminiumspecies V with an organometallic reagent or hydride (if R4═H). Ifappropriate, the iminium species V may be isolated. The reaction isperformed preferably in an ethereal solvent and at temperatures between−78° C. and 40° C., more preferably at −15° C. or at room temperature aspreviously described (see for example Tetrahedron Letters 52(2),281-284, 2011 or Journal of Organic Chemistry, 70(5), 1930-1933, 2005).

Compounds IV are either commercially available or can be accessedthrough known methods that are obvious for a person skilled in the art.

The compounds of the formula I or compositions comprising said compoundsaccording to the invention and the mixtures comprising said compoundsand compositions, respectively, are suitable as fungicides. They aredistinguished by an outstanding effectiveness against a broad spectrumof phytopathogenic fungi, including soil-borne fungi, which deriveespecially from the following classes or are closely related to any ofthem: Ascomycota (Ascomycetes), for example, but not limited to thegenus Cocholiobolus, Colletotrichum, Fusarium, Microdochium,Penicillium, Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella;Basdiomycota (Basidiomycetes), for example, but not limited to the genusPhakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, andUstilago; Chytridiomycota (Chytridiomycetes), for example, but notlimited to the genus Chytridiales, and Synchytrium; Deuteromycetes (syn.Fungi imperfecti), for example, but not limited to the genus Ascochyta,Diplock's, Erysiphe, Fusarium, Phomopsis, and Pyrenophora;Peronosporomycetes (syn. Oomycetes), for example but not limited to thegenus Peronospora, Pythium, Phytophthora; Plasmodiophoromycetes, forexample but not limited to the genus Plasmodiophora; Zygomycetes, forexample, but not limited to the genus Rhizopus.

Some of the compounds of the formula I and the compositions according tothe invention are systemically effective and they can be used in cropprotection as foliar fungicides, fungicides for seed dressing and soilfungicides. Moreover, they are suitable for controlling harmful fungi,which inter alia occur in wood or roots of plants.

The compounds I and the compositions according to the invention areparticularly important in the control of a multitude of phytopathogenicfungi on various cultivated plants, such as cereals, e. g. wheat, rye,barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet;fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears,plums, peaches, almonds, cherries, strawberries, raspberries,blackberries or gooseberries; leguminous plants, such as lentils, peas,alfalfa or soybeans; oil plants, such as rape, mustard, olives,sunflowers, coconut, cocoa beans, castor oil plants, oil palms, groundnuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiberplants, such as cotton, flax, hemp or jute; citrus fruit, such asoranges, lemons, grapefruits or mandarins; vegetables, such as spinach,lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes,cucurbits or paprika; lauraceous plants, such as avocados, cinnamon orcamphor; energy and raw material plants, such as corn, soybean, rape,sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines(table grapes and grape juice grape vines); hop; turf; sweet leaf (alsocalled Stevia); natural rubber plants or ornamental and forestry plants,such as flowers, shrubs, broad-leaved trees or evergreens, e. g.conifers; and on the plant propagation material, such as seeds, and thecrop material of these plants. Preferably, compounds I and compositionsthereof, respectively are used for controlling a multitude of fungi onfield crops, such as potatoes sugar beets, tobacco, wheat, rye, barley,oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee orsugar cane; fruits; vines; ornamentals; or vegetables, such ascucumbers, tomatoes, beans or squashes. The term “plant propagationmaterial” is to be understood to denote all the generative parts of theplant such as seeds and vegetative plant material such as cuttings andtubers (e. g. potatoes), which can be used for the multiplication of theplant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes,shoots, sprouts and other parts of plants, including seedlings and youngplants, which are to be transplanted after germination or afteremergence from soil. These young plants may also be protected beforetransplantation by a total or partial treatment by immersion or pouring.

Preferably, treatment of plant propagation materials with compounds Iand compositions thereof, respectively, is used for controlling amultitude of fungi on cereals, such as wheat, rye, barley and oats;rice, corn, cotton and soybeans.

The term “cultivated plants” is to be understood as including plantswhich have been modified by breeding, mutagenesis or genetic engineeringincluding but not limiting to agricultural biotech products on themarket or in development (cf. http://cera-gmc.org/, see GM crop databasetherein). Genetically modified plants are plants, which genetic materialhas been so modified by the use of recombinant DNA techniques that undernatural circumstances cannot readily be obtained by cross breeding,mutations or natural recombination. Typically, one or more genes havebeen integrated into the genetic material of a genetically modifiedplant in order to improve certain properties of the plant. Such geneticmodifications also include but are not limited to targetedpost-translational modification of protein(s), oligo- or polypeptides e.g. by glycosylation or polymer additions such as prenylated, acetylatedor farnesylated moieties or PEG moieties. Plants that have been modifiedby breeding, mutagenesis or genetic engineering, e. g. have beenrendered tolerant to applications of specific classes of herbicides,such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicidessuch as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoenedesaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors suchas sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphatesynthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase(GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidaseinhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase(ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicidesas a result of conventional methods of breeding or genetic engineering.Furthermore, plants have been made resistant to multiple classes ofherbicides through multiple genetic modifications, such as resistance toboth glyphosate and glufosinate or to both glyphosate and a herbicidefrom another class such as ALS inhibitors, HPPD inhibitors, auxinherbicides, or ACCase inhibitors. These herbicide resistancetechnologies are e. g. described in Pest Managem. Sci. 61, 2005, 246;61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008,326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res.58, 2007, 708; Science 316, 2007, 1185; and references quoted therein.Several cultivated plants have been rendered tolerant to herbicides byconventional methods of breeding (mutagenesis), e. g. Clearfield® summerrape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant tosulfonyl ureas, e. g. tribenuron. Genetic engineering methods have beenused to render cultivated plants such as soybean, cotton, corn, beetsand rape, tolerant to herbicides such as glyphosate and glufosinate,some of which are commercially available under the trade namesRoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance®(imidazolinone tolerant, BASF SE, Germany) and LibertyLink®(glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as δ-endotoxins, e. g. CryIA(b),CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e. g.Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilbene synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e. g. WO 02/015701). Further examples of such toxins orgenetically modified plants capable of synthesizing such toxins aredisclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451 878, WO 03/18810 and WO 03/52073. The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above. These insecticidal proteins contained in thegenetically modified plants impart to the plants producing theseproteins tolerance to harmful pests from all taxonomic groups ofarthropods, especially to beetles (Coeloptera), two-winged insects(Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).Genetically modified plants capable to synthesize one or moreinsecticidal proteins are, e. g., described in the publicationsmentioned above, and some of which are commercially available such asYieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus(corn cultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corncultivars producing the Cry9c toxin), Herculex® RW (corn cultivarsproducing Cry34Ab1, Cry35Ab1 and the enzymephosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf) (potato cultivars producing the Cry3A toxin);Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g.Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enyzme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the Cry1F toxin and PAT enzyme). Furthermore,plants are also covered that are by the use of recombinant DNAtechniques capable to synthesize one or more proteins to increase theresistance or tolerance of those plants to bacterial, viral or fungalpathogens. Examples of such proteins are the so-called“pathogenesis-related proteins” (PR proteins, see, e. g. EP-A 392 225),plant disease resistance genes (e. g. potato cultivars, which expressresistance genes acting against Phytophthora infestans derived from theMexican wild potato Solarium bulbocastanum) or T4-lysozym (e. g. potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e. g. bio mass production, grain yield, starchcontent, oil content or protein content), tolerance to drought, salinityor other growth-limiting environmental factors or tolerance to pests andfungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve human or animalnutrition, e. g. oil crops that produce health-promoting long-chainomega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera®rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve raw materialproduction, e. g. potatoes that produce increased amounts of amylopectin(e. g. Amflora® potato, BASF SE, Germany).

The compounds I and compositions thereof, respectively, are particularlysuitable for controlling the following plant diseases:

Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. candida)and sunflowers (e. g. A. tragopogonis); Altemaria spp. (Alternaria leafspot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A.tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A.altemata), tomatoes (e. g. A. solani or A. altemata) and wheat;Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. oncereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A.hordei on barley; Bipolaris and Drechslera spp. (teleomorph:Cochliobolus spp.), e. g. Southern leaf blight (D. maydls) or Northernleaf blight (B. zeicola) on corn, e. g. spot blotch (B. soroklnlana) oncereals and e. g. B. oryzae on rice and turfs; Blumeria (formerlyErysiphe) graminis (powdery mildew) on cereals (e. g. on wheat orbarley); Botrytis cinerea (teleomorph: Botryotinia fucliana: grey mold)on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce,carrots, celery and cabbages), rape, flowers, vines, forestry plants andwheat; Bremla lactucae (downy mildew) on lettuce; Ceratocystis (syn.Ophlostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leafspots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets(e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C.sojina or C. kikuchil) and rice; Cladosporlum spp. on tomatoes (e. g. C.fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat;Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph:Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum),cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C.miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph:Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypil), corn (e.g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g.C. coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans(e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C.sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) onsoybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olivetrees; Cylindrocarpon spp. (e. g. fruit tree canker or young vinedecline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines(e. g. C. liriodendri, teleomorph: Neonectria liriodendri, Black FootDisease) and ornamentals; Dematophora (teleomorph: Rosellinla) necatrbc(root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum(damping off) on soybeans; Drechslera (syn. Helminthosporium,teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D.teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), riceand turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia(syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora(earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilumand/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri),soft fruits (E. veneta: anthracnose) and vines (E. ampelina:anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (blackmold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E.betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E.cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata(Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertellablepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn.Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium(teleomorph: Gibberella) spp. (wilt, root or stem rot) on variousplants, such as F. gram.nearum or F. culmorum (root rot, scab or headblight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F.solani (f. sp. glycines now syn. F. virguliforme) and F. tucumaniae andF. brasilierase each causing sudden death syndrome on soybeans, and F.verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals(e. g. wheat or barley) and corn; Glomerella spp. on cereals (e. g. G.zeae) and rice (e. g. G. fujikuroi, Bakanae disease); Glomerellacingulata on vines, pome fruits and other plants and G. gossypii oncotton; Grainstaining complex on rice; Guignardia bidwellii (black rot)on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g.G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera,teleomorph: Cochliobolus) on corn, cereals and rice; Hemlleia spp., e.g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora(syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn.phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn.Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley);Microsphaera diffusa (powdery mildew) on soybeans; Monllinia spp., e. g.M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brownrot) on stone fruits and other rosaceous plants; Mycosphaerella spp. oncereals, bananas, soft fruits and ground nuts, such as e. g. M.graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M.fifiensis (black Sigatoka disease) on bananas; Peronospora spp. (downymildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica),onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g.P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) onsoybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphlla and P.tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam(root and stem rot) on rape and cabbage and P. betae (root rot, leafspot and damping-off) on sugar beets; Phomopsis spp. on sunflowers,vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stemrot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis(brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit andstem root) on various plants, such as paprika and cucurbits (e. g. P.capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes andtomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g.P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) oncabbage, rape, radish and other plants; Plasmopara spp., e. g. P.viticola (grapevine downy mildew) on vines and P. halstedii onsunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop,pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e.g. on cereals, such as barley and wheat (P. graminis) and sugar beets(P. betae) and thereby transmitted viral diseases; Pseudocercosporellaherpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e.g. wheat or barley; Pseudoperonospora (downy mildew) on various plants,e. g. P. cubensis on cucurbits or P. humili on hop; Pseudopeziculatracheiphlla (red fire disease or, rotbrenner', anamorph: Phialophora)on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina(brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei(dwarf rust), P. graminis (stem or black rust) or P. recondita (brown orleaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii(orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora(anamorph: Drechslera) tritici-repengs (tan spot) on wheat or P. teres(net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph:Magnaporthe grisea, rice blast) on rice and P. grisea on turf andcereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton,rape, sunflowers, soybeans, sugar beets, vegetables and various otherplants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R.collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barleyand R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice,potatoes, turf, corn, rape, potatoes, sugar beets, vegetables andvarious other plants, e. g. R. solani (root and stem rot) on soybeans,R. solani (sheath blight) on rice or R. cereaks (Rhizoctonia springblight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot)on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporiumsecallis (scald) on barley, rye and triticale; Sarocladium oryzae and S.attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or whitemold) on vegetables and field crops, such as rape, sunflowers (e. g. S.sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum);Septoria spp. on various plants, e. g. S. glycines (brown spot) onsoybeans, S. tritici (Septoria blotch) on wheat and S. (syn.Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn.Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines;Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn.Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn,(e. g. S. reiliana: head smut), sorghum and sugar cane; Sphaerothecafuliginea (powdery mildew) on cucurbits; Spongospora subterranea(powdery scab) on potatoes and thereby transmitted viral diseases;Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch,teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat;Synchytrium endobioticum on potatoes (potato wart disease); Taphrinaspp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni(plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco,pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn.Chalara elegans); Tilletia spp. (common bunt or stinking smut) oncereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T.controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) onbarley or wheat; Urocysgs spp., e. g. U. occulta (stem smut) on rye;Uromyces spp. (rust) on vegetables, such as beans (e. g. U.appencliculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae);Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae),corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab)on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt)on various plants, such as fruits and ornamentals, vines, soft fruits,vegetables and field crops, e. g. V. dahliae on strawberries, rape,potatoes and tomatoes. In a preferred embodiment the compounds I andcompositions thereof, respectively, are particularly suitable forcontrolling the following plant diseases: Puccinia spp. (rusts) onvarious plants, for example, but not limited to P. triticina (brown orleaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarfrust), P. graminis (stem or black rust) or P. recondita (brown or leafrust) on cereals, such as e. g. wheat, barley or rye and Phakopsoraceaespp. on various plants, in particular Phakopsora pachyrhizi and P.meibomiae (soybean rust) on soybeans.

The compounds I and compositions thereof, respectively, are alsosuitable for controlling harmful fungi in the protection of storedproducts or harvest and in the protection of materials. The term“protection of materials” is to be understood to denote the protectionof technical and non-living materials, such as adhesives, glues, wood,paper and paperboard, textiles, leather, paint dispersions, plastics,cooling lubricants, fiber or fabrics, against the infestation anddestruction by harmful microorganisms, such as fungi and bacteria. As tothe protection of wood and other materials, the particular attention ispaid to the following harmful fungi: Ascomycetes such as Ophiostomaspp., Ceratocysgs spp., Aureobasidium pullulans, Scierophoma spp.,Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.;Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllumspp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. andTyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporiumspp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecllomycesspp. and Zygomycetes such as Mucor spp., and in addition in theprotection of stored products and harvest the following yeast fungi areworthy of note: Candida spp. and Saccharomyces cerevisae. The method oftreatment according to the invention can also be used in the field ofprotecting stored products or harvest against attack of fungi andmicroorganisms. According to the present invention, the term “storedproducts” is understood to denote natural substances of plant or animalorigin and their processed forms, which have been taken from the naturallife cycle and for which long-term protection is desired. Storedproducts of crop plant origin, such as plants or parts thereof, forexample stalks, leafs, tubers, seeds, fruits or grains, can be protectedin the freshly harvested state or in processed form, such as pre-dried,moistened, comminuted, ground, pressed or roasted, which process is alsoknown as post-harvest treatment. Also falling under the definition ofstored products is timber, whether in the form of crude timber, such asconstruction timber, electricity pylons and barriers, or in the form offinished articles, such as furniture or objects made from wood. Storedproducts of animal origin are hides, leather, furs, hairs and the like.The combinations according the present invention can preventdisadvantageous effects such as decay, discoloration or mold. Preferably“stored products” is understood to denote natural substances of plantorigin and their processed forms, more preferably fruits and theirprocessed forms, such as pomes, stone fruits, soft fruits and citrusfruits and their processed forms.

The compounds of formula I can be present in different crystalmodifications whose biological activity may differ. They are likewisesubject matter of the present invention.

The compounds I are employed as such or in form of compositions bytreating the fungi or the plants, plant propagation materials, such asseeds, soil, surfaces, materials or rooms to be protected from fungalattack with a fungicidally effective amount of the active substances.The application can be carried out both before and after the infectionof the plants, plant propagation materials, such as seeds, soil,surfaces, materials or rooms by the fungi.

Plant propagation materials may be treated with compounds I as such or acomposition comprising at least one compound I prophylactically eitherat or before planting or transplanting. The invention also relates toagrochemical compositions comprising an auxiliary and at least onecompound I according to the invention.

An agrochemical composition comprises a fungicidally effective amount ofa compound I. The term “effective amount” denotes an amount of thecomposition or of the compounds I, which is sufficient for controllingharmful fungi on cultivated plants or in the protection of materials andwhich does not result in a substantial damage to the treated plants.Such an amount can vary in a broad range and is dependent on variousfactors, such as the fungal species to be controlled, the treatedcultivated plant or material, the climatic conditions and the specificcompound I used.

The compounds I, their N-oxides and salts can be converted intocustomary types of agrochemical compositions, e. g. solutions,emulsions, suspensions, dusts, powders, pastes, granules, pressings,capsules, and mixtures thereof. Examples for composition types aresuspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC),emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes,pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS),pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG),insecticidal articles (e. g. LN), as well as gel formulations for thetreatment of plant propagation materials such as seeds (e. g. GF). Theseand further compositions types are defined in the “Catalogue ofpesticide formulation types and international coding system”, TechnicalMonograph No. 2, 6th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e. g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol,propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones,e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixturesthereof. Suitable solid carriers or fillers are mineral earths, e. g.silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays,dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesiumsulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch;fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas; products of vegetable origin, e. g. cereal meal, treebark meal, wood meal, nutshell meal, and mixtures thereof. Suitablesurfactants are surface-active compounds, such as anionic, cationic,nonionic and amphoteric surfactants, block polymers, polyelectrolytes,and mixtures thereof. Such surfactants can be used as emulsifier,dispersant, solubilizer, wetter, penetration enhancer, protectivecolloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylaryl sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates offatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonatesof alkoxylated arylphenols, sulfonates of condensed naphthalenes,sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenesand alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examplesof sulfates are sulfates of fatty acids and oils, of ethoxylatedalkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acidesters. Examples of phosphates are phosphate esters. Examples ofcarboxylates are alkyl carboxylates, and carboxylated alcohol oralkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinyl amines or polyethylene amines.

Suitable adjuvants are compounds, which have a negligible or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxiliaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e. g. xanthan gum,carboxymethyl cellulose), inorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e. g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e. g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e. g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or syntheticwaxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-Soluble Concentrates (SL, LS)

10-60 wt % of a compound I and 5-15 wt % wetting agent (e. g. alcoholalkoxylates) are dissolved in water and/or in a water-soluble solvent(e. g. alcohols) ad 100 wt %. The active substance dissolves upondilution with water.

ii) Dispersible Concentrates (DC)

5-25 wt % of a compound I and 1-10 wt % dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad100 wt %. Dilution with water gives a dispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt % of a compound I and 5-10 wt % emulsifiers (e. g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved inwater-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I and 1-10 wt % emulsifiers (e. g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in20-40 wt % water-insoluble organic solvent (e. g. aromatic hydrocarbon).This mixture is introduced into water ad 100 wt % by means of anemulsifying machine and made into a homogeneous emulsion. Dilution withwater gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I are comminuted withaddition of 2-10 wt % dispersants and wetting agents (e. g. sodiumlignosulfonate and alcohol ethoxylate), 0.1-2 wt % thickener (e. g.xanthan gum) and water ad 100 wt % to give a fine active substancesuspension. Dilution with water gives a stable suspension of the activesubstance. For FS type composition up to 40 wt % binder (e. g. polyvinylalcohol) is added.

vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50-80 wt % of a compound I are ground finely with addition ofdispersants and wetting agents (e. g. sodium lignosulfonate and alcoholethoxylate) ad 100 wt % and prepared as water-dispersible orwater-soluble granules by means of technical appliances (e. g.extrusion, spray tower, fluidized bed). Dilution with water gives astable dispersion or solution of the active substance.

vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, WS)

50-80 wt % of a compound I are ground in a rotor-stator mill withaddition of 1-5 wt % dispersants (e. g. sodium lignosulfonate), 1-3 wt %wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g.silica gel) ad 100 wt %. Dilution with water gives a stable dispersionor solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a compound I are comminuted withaddition of 3-10 wt % dispersants (e. g. sodium lignosulfonate), 1-5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt % togive a fine suspension of the active substance. Dilution with watergives a stable suspension of the active substance.

ix) Microemulsion (ME)

5-20 wt % of a compound I are added to 5-30 wt % organic solvent blend(e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt %surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate),and water ad 100%. This mixture is stirred for 1 h to producespontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I, 0-40 wt % waterinsoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt %acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di-or triacrylate) are dispersed into an aqueous solution of a protectivecolloid (e. g. polyvinyl alcohol). Radical polymerization results in theformation of poly(meth)acrylate microcapsules. Alternatively, an oilphase comprising 5-50 wt % of a compound I according to the invention,0-40 wt % water insoluble organic solvent (e. g. aromatic hydrocarbon),and an isocyanate monomer (e. g. diphenylmethene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e. g.polyvinyl alcohol). The addition of a polyamine (e. g.hexamethylenediamine) results in the formation of polyureamicrocapsules. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.

xi) Dustable Powders (DP, DS)

1-10 wt % of a compound I are ground finely and mixed intimately withsolid carrier (e. g. finely divided kaolin) ad 100 wt %.

xii) Granules (GR, FG)

0.5-30 wt % of a compound I is ground finely and associated with solidcarrier (e. g. silicate) ad 100 wt %. Granulation is achieved byextrusion, spray-drying or fluidized bed.

xiii) Ultra-Low Volume Liquids (UL)

1-50 wt % of a compound I are dissolved in organic solvent (e. g.aromatic hydrocarbon) ad 100 wt %.

The compositions types i) to xiii) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, more preferably between 1 and 70%, andin particular between 10 and 60%, by weight of active substance. Theactive substances are employed in a purity of from 90% to 100%,preferably from 95% to 100% (according to NMR spectrum).

For the purposes of treatment of plant propagation materials,particularly seeds, solutions for seed treatment (LS), Suspoemulsions(SE), flowable concentrates (FS), powders for dry treatment (DS),water-dispersible powders for slurry treatment (WS), water-solublepowders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels(GF) are usually employed. The compositions in question give, aftertwo-to-tenfold dilution, active substance concentrations of from 0.01 to60% by weight, preferably from 0.1 to 40%, in the ready-to-usepreparations. Application can be carried out before or during sowing.Methods for applying compound I and compositions thereof, respectively,onto plant propagation material, especially seeds, include dressing,coating, pelleting, dusting, and soaking as well as in-furrowapplication methods. Preferably, compound I or the compositions thereof,respectively, are applied on to the plant propagation material by amethod such that germination is not induced, e. g. by seed dressing,pelleting, coating and dusting.

When employed in plant protection, the amounts of active substancesapplied are, depending on the kind of effect desired, from 0.001 to 2 kgper ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha. Intreatment of plant propagation materials such as seeds, e. g. bydusting, coating or drenching seed, amounts of active substance of from0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to100 g and most preferably from 5 to 100 g, per 100 kilogram of plantpropagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amountof active substance applied depends on the kind of application area andon the desired effect. Amounts customarily applied in the protection ofmaterials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of activesubstance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e. g. herbicides, insecticides,fungicides, growth regulators, safeners, biopesticides) may be added tothe active substances or the compositions comprising them as premix or,if appropriate not until immediately prior to use (tank mix). Theseagents can be admixed with the compositions according to the inventionin a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

A pesticide is generally a chemical or biological agent (such aspestidal active ingredient, compound, composition, virus, bacterium,antimicrobial or disinfectant) that through its effect deters,incapacitates, kills or otherwise discourages pests. Target pests caninclude insects, plant pathogens, weeds, mollusks, birds, mammals, fish,nematodes (roundworms), and microbes that destroy property, causenuisance, spread disease or are vectors for disease. The term“pesticide” includes also plant growth regulators that alter theexpected growth, flowering, or reproduction rate of plants; defoliantsthat cause leaves or other foliage to drop from a plant, usually tofacilitate harvest; desiccants that promote drying of living tissues,such as unwanted plant tops; plant activators that activate plantphysiology for defense of against certain pests; safeners that reduceunwanted herbicidal action of pesticides on crop plants; and plantgrowth promoters that affect plant physiology e.g. to increase plantgrowth, biomass, yield or any other quality parameter of the harvestablegoods of a crop plant.

The user applies the composition according to the invention usually froma predosage device, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank orany other kind of vessel used for applications (e. g. seed treaterdrums, seed pelleting machinery, knapsack sprayer) and furtherauxiliaries may be added, if appropriate.

Consequently, one embodiment of the invention is a kit for preparing ausable pesticidal composition, the kit comprising a) a compositioncomprising component 1) as defined herein and at least one auxiliary;and b) a composition comprising component 2) as defined herein and atleast one auxiliary; and optionally c) a composition comprising at leastone auxiliary and optionally a further active component 3) as definedherein.

Mixing the compounds I or the compositions comprising them in the useform as fungicides with other fungicides results in many cases in anexpansion of the fungicidal spectrum of activity being obtained or in aprevention of fungicide resistance development. Furthermore, in manycases, synergistic effects are obtained.

The following list of pesticides II (e. g. pesticidally-activesubstances and biopesticides), in conjunction with which the compounds Ican be used, is intended to illustrate the possible combinations butdoes not limit them:

A) Respiration inhibitors: Inhibitors of complex III at Q_(o) site:azoxystrobin (A.1.1), coumeth-oxystrobin (A.1.2), coumoxystrobin(A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin(A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8),kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin(A.1.11), orysastrobin (A.1.12), picoxy-strobin (A.1.13), pyraclostrobin(A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16),trifloxystrobin (A.1.17),2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide(A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1.20),famoxadone (A.1.21), fenamidone (A.1.21),methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxy]methyl]phenyl]-N-methoxy-carbamate(A.1.22),1-[3-chloro-2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one(A.1.23),1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one(A.1.24),1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetra-zol-5-one(A.1.25),1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one(A.1.26),1-[2-[[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one(A.1.27),1-[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one(A.1.28),1-[3-chloro-2-[[4-(p-tolypthiazol-2-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one(A.1.29),1-[3-cyclopropyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]-methyl]phenyl]-4-methyl-tetrazol-5-one(A.1.30),1-[3-(difluoromethoxy)-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one(A.1.31),1-methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one(A.1.32),1-methyl-4-[3-methyl-2-[[1-[3-(trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one(A.1.33),(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide(A.1.34),(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide(A.1.35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37),2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acidmethylester (A.1.38).

Inhibitors of complex III at Q_(i) site: cyazofamid (A.2.1), amisulbrom(A.2.2),[(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate (A.2.3),[2-[[(7R,8R,9S)-7-benzyl-9-methyl-8-(2-methylpropanoyloxy)-2,6-dioxo-1,5-dioxonan-3-yl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl2-methylpropanoate (A.2.4),[(6S,7R,8R)-8-benzyl-3-[[4-methoxy-3-(propanoyloxy-methoxy)pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate (A.2.5).

Inhibitors of complex II: benodanil (A.3.1), benzovindiflupyr (A.3.2),bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6),fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr(A.3.10), isofetamid (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13),oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16),3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenypethyl]pyrazole-4-carboxamide(A.3.17),N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide(A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide(A.3.21),3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(A.3.22),3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(A.3.23),1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(A.3.24),3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(A.3.25),1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(A.3.26),3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(A.3.27),3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide(A.3.28), methyl(E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate(A.3.30),N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5fluoro-1-methyl-pyrazole-4-carboxamide (A.3.31),2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide(A.3.32),2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide(A.3.33),2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)¬pyridine-3-carboxamide(A.3.34),2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]¬pyridine-3-carboxamide(A.3.35),2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)¬py¬iridine-3-carboxamide(A.3.36),2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]¬pyridine-3-carboxamide(A.3.37),2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)¬pyridine-3-carboxamide(A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4yl]pyridine-3-carboxamide (A.3.39).

Other respiration inhibitors: diflumetorim (A.4.1); nitrophenylderivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4),fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometalcompounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride(A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam(A.4.12).

B) Sterol biosynthesis inhibitors (SBI fungicides)

C14 demethylase inhibitors: triazoles: azaconazole (B.1.1), bitertanol(B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole(B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole(B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole(B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole(B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil(B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole(B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole(B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon(B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole(B.1.30),1-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H-[1,2,4]triazole(B.1.31),2-[rel-(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol(B.1.32),2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol(B.1.33),1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol(B.1.34),2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol(B.1.35),2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol(B.1.36),2-[4-(4-chloro-phenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol(B.1.37),2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol(B.1.38),2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol(B.1.39),2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol(B.1.40),2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol(B.1.41),2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol(B.1.42),2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol(B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45),prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines, pyridines andpiperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51),[3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenypisoxazol-4-yl]-(3-pyridyl)methanol(B.1.52).

Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph (B.2.2),dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5),fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8).

Inhibitors of 3-keto reductase: fenhexamid (B.3.1).

Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1).

C) Nucleic acid synthesis inhibitors

Phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1),benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M(C.1.5), ofurace (C.1.6), oxadixyl (C.1.7). Other nucleic acid synthesisinhibitors: hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid(C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5),5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6),5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7),5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8).

D) Inhibitors of cell division and cytoskeleton

Tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole(D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5),3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (D.1.6),3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1.7),N-ethyl-2-[(3-ethynyl-8-methyl-6-q uinolyl)oxy]butanamide (D.1.8),N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9),2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide(D.1.10),2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide(D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide(D.1.12),2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide(D.1.13),2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide(D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15),4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine(D.1.16). Other cell division inhibitors: diethofencarb (D.2.1),ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide(D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7).

E) Inhibitors of amino acid and protein synthesis

Methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim(E.1.2), pyrimethanil (E.1.3). Protein synthesis inhibitors:blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycinhydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin(E.2.5), oxytetracyclin (E.2.6).

F) Signal transduction inhibitors

MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2),procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5).

G protein inhibitors: quinoxyfen (F.2.1).

G) Lipid and membrane synthesis inhibitors

Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos(G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4).

Lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene(G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6),etridiazole (G.2.7).

Phospholipid biosynthesis and cell wall deposition: dimethomorph(G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4),benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7).

Compounds affecting cell membrane permeability and fatty acides:propamocarb (G.4.1). Inhibitors of oxysterol binding protein:oxathiapiprolin (G.5.1),2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate (G.5.2),2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate (G.5.3),4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide(G.5.4),4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide(G.5.5),4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide(G.5.6),4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide(G.5.7),4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide(G.5.8),4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyppyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide(G.5.9),4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide(G.5.10),(4-[1-[2-[5-cyclopropyl-3-(trifluoromethyppyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide(G.5.11).

H) Inhibitors with Multi Site Action

Inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2),copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride(H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7).

Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb(H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram(H.2.7), zineb (H.2.8), ziram (H.2.9). Organochlorine compounds:anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan(H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7),hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts,phthalide (H.3.10), tolylfluanid (H.3.11). Guanidines and others:guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine(H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6),iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8),dithianon (H.4.9),2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone(H.4.10).

I) Cell wall synthesis inhibitors

Inhibitors of glucan synthesis: validamycin (I.1.1), polyoxin B (I.1.2).

Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2),carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5).

J) Plant defence inducers

Acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3),tiadinil (J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl(J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts(J.1.8), potassium or sodium bicarbonate (J.1.9),4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10).

K) Unknown mode of action

Bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3),cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocymet(K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9),di-fenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11), fenitropan(K.1.12), fenpyrazamine (K.1.13), flumetover (K.1.14), flusulfamide(K.1.15), flutianil (K.1.16), harpin (K.1.17), metha-sulfocarb (K.1.18),nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21),oxin-copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24),tecloftalam (K.1.25), triazoxide (K.1.26),N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine (K.1.27),N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine (K.1.28),N′-[4-[[3-[(4-chlorophenyhmethyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine(K.1.29),N′-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine(K.1.30),N′-[5-bromo-6-[1-(3,5-difluorophenyhethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine(K.1.31),N′-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine(K.1.32),N′-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine(K.1.33),N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.34),N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.35),2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide(K.1.36),3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine(pyrisoxazole) (K.1.37),3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine (K.1.38),5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole(K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40),picarbutrazox (K.1.41), pentylN-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate(K.1.42), but-3-ynylN-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate(K.1.43),2-[2-[(7,8-difluoro-2-methyl-3-quinolyhoxy]-6-fluoro-phenyl]propan-2-ol(K.1.44),2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol(K.1.45),3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yhquinoline(K.1.46), quinofumelin (K.1.47),3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline(K.1.48), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine(K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50),2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline(K.1.51), 3-[(3,4-dichloroisothiazol-5-yl)methoxy]-1,2-benzothiazole1,1-dioxide (K.1.52),N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine(K.1.53).

M) Growth regulators

abscisic acid (M.1.1), amidochlor, ancymidol, 6-benzylaminopurine,brassinolide, butralin, chlormequat, chlormequat chloride, cholinechloride, cyclanilide, daminozide, dikegulac, dimethipin,2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet,forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid,maleic hydrazide, mefluidide, mepiquat, mepiquat chloride,naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione,prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol,tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid,trinexapac-ethyl and uniconazole;

N) Herbicides from classes N.1 to N.15

N.1 Lipid biosynthesis inhibitors: alloxydim (N.1.1), alloxydim-sodium(N.1.2), butroxydim (N.1.3), clethodim (N.1.4), clodinafop (N.1.5),clodinafop-propargyl (N.1.6), cycloxydim (N.1.7), cyhalofop (N.1.8),cyhalofop-butyl (N.1.9), diclofop(N.1.10), diclofop-methyl (N.1.11),fenoxaprop (N.1.12), fenoxaprop-ethyl (N.1.13), fenoxaprop-P (N.1.14),fenoxaprop-P-ethyl (N.1.15), fluazifop (N.1.16), fluazifop-butyl(N.1.17), fluazifop-P (N.1.18), fluazifop-P-butyl (N.1.19), haloxyfop(N.1.20), haloxyfop-methyl (N.1.21), haloxyfop-P (N.1.22),haloxyfop-P-methyl (N.1.23), metamifop (N.1.24), pinoxaden (N.1.25),profoxydim (N.1.26), propaquizafop (N.1.27), quizalofop (N.1.28),quizalofop-ethyl (N.1.29), quizalofop-tefuryl (N.1.30), quizalofop-P(N.1.31), quizalofop-P-ethyl (N.1.32), quizalofop-P-tefuryl (N.1.33),sethoxydim (N.1.34), tepraloxydim (N.1.35), tralkoxydim (N.1.36),4-(4′-chloro-4-cyclo¬propyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one((N.1.37) CAS 1312337-72-6);4-(2′,4′-dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one((N.1.38) CAS 1312337-45-3);4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one((N.1.39) CAS 1033757-93-5);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione((N.1.40) CAS 1312340-84-3);5-(acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one((N.1.41) CAS 1312337-48-6);5-(acetyloxy)-4-(2″,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(N.1.42);5-(acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one((N.1.43) CAS 1312340-82-1);5-(acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one((N.1.44) CAS 1033760-55-2);4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester ((N.1.45) CAS 1312337-51-1);4-(2″,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (N.1.46);4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester ((N.1.47) CAS 1312340-83-2);4-(2′,4′-dichloro-4-ethyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester ((N.1.48) CAS 1033760-58-5); benfuresate(N.1.49), butylate (N.1.50), cycloate (N.1.51), dalapon (N.1.52),dimepiperate (N.1.53), EPTC (N.1.54), esprocarb (N.1.55), ethofumesate(N.1.56), flupropanate (N.1.57), molinate (N.1.58), orbencarb (N.1.59),pebulate (N.1.60), prosulfocarb (N.1.61), TCA (N.1.62), thiobencarb(N.1.63), tiocarbazil (N.1.64), triallate (N.1.65) and vernolate(N.1.66);

N.2 ALS inhibitors: amidosulfuron (N.2.1), azimsulfuron (N.2.2),bensulfuron (N.2.3), bensul-furon-methyl (N.2.4), chlorimuron (N.2.5),chlorimuron-ethyl (N.2.6), chlorsulfuron (N.2.7), cinosulfuron (N.2.8),cyclosulfamuron (N.2.9), ethametsulfuron (N.2.10),ethametsulfuron-methyl (N.2.11), ethoxysulfuron (N.2.12), flazasulfuron(N.2.13), flucetosulfuron (N.2.14), flupyrsulfuron (N.2.15),flupyrsulfuron-methyl-sodium (N.2.16), foramsulfuron (N.2.17),halosulfuron (N.2.18), halosulfuron-methyl (N.2.19), imazosulfuron(N.2.20), iodosulfuron (N.2.21), iodosulfuron-methyl-sodium (N.2.22),iofensulfuron (N.2.23), iofensulfuron-sodium (N.2.24), mesosulfuron(N.2.25), metazosulfuron (N.2.26), metsulfuron (N.2.27),metsulfuron-methyl (N.2.28), nicosulfuron (N.2.29), orthosulfamuron(N.2.30), oxasulfuron (N.2.31), primisulfuron (N.2.32),primisulfuron-methyl (N.2.33), propyrisulfuron (N.2.34), prosulfuron(N.2.35), pyrazosulfuron (N.2.36), pyrazosulfuron-ethyl (N.2.37),rimsulfuron (N.2.38), sulfometuron (N.2.39), sulfometuron-methyl(N.2.40), sulfosulfuron (N.2.41), thifensulfuron (N.2.42),thifensulfuron-methyl (N.2.43), triasulfuron (N.2.44), tribenuron(N.2.45), tribenuron-methyl (N.2.46), trifloxysulfuron (N.2.47),triflusulfuron (N.2.48), triflusulfuron-methyl (N.2.49), tritosulfuron(N.2.50), imazamethabenz (N.2.51), imazamethabenz-methyl (N.2.52),imazamox (N.2.53), imazapic (N.2.54), imazapyr (N.2.55), imazaquin(N.2.56), imazethapyr (N.2.57); cloransulam (N.2.58), cloransulam-methyl(N.2.59), diclosulam (N.2.60), flumetsulam (N.2.61), florasulam(N.2.62), metosulam (N.2.63), penoxsulam (N.2.64), pyrimisulfan (N.2.65)and pyroxsulam (N.2.66); bispyribac (N.2.67), bispyribac-sodium(N.2.68), pyribenzoxim (N.2.69), pyriftalid (N.2.70), pyriminobac(N.2.71), pyriminobac-methyl (N.2.72), pyrithiobac (N.2.73),pyrithiobac-sodium (N.2.74),4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid-1-methyhethyl ester ((N.2.75) CAS 420138-41-6),4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]¬methyl]amino]-benzoicacid propyl ester ((N.2.76) CAS 420138-40-5),N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine((N.2.77) CAS 420138-01-8); flucarbazone (N.2.78), flucarbazone-sodium(N.2.79), propoxycarbazone (N.2.80), propoxycarbazone-sodium (N.2.81),thiencarbazone (N.2.82), thiencarbazone-methyl (N.2.83), triafamone(N.2.84);

N.3 Photosynthesis inhibitors: amicarbazone (N.3.1); chlorotriazine(N.3.2); ametryn (N.3.3), atrazine (N.3.4), chloridazone (N.3.5),cyanazine (N.3.6), desmetryn (N.3.7), dimethametryn (N.3.8), hexazinone(N.3.9), metribuzin (N.3.10), prometon (N.3.11), prometryn (N.3.12),pro-pazine (N.3.13), simazine (N.3.14), simetryn (N.3.15), terbumeton(N.3.16), terbuthylazin (N.3.17), terbutryn (N.3.18), trietazin(N.3.19); chlorobromuron (N.3.20), chlorotoluron (N.3.21), chloroxuron(N.3.22), dimefuron (N.3.23), diuron (N.3.24), fluometuron (N.3.25),isoproturon (N.3.26), isouron (N.3.27), linuron (N.3.28), metamitron(N.3.29), methabenzthiazuron (N.3.30), metobenzuron (N.3.31), metoxuron(N.3.32), monolinuron (N.3.33), neburon (N.3.34), siduron (N.3.35),tebuthiuron (N.3.36), thiadiazuron (N.3.37), desmedipham (N.3.38),karbutilat (N.3.39), phenmedipham (N.3.40), phenmedipham-ethyl (N.3.41),bromofenoxim (N.3.42), bromoxynil (N.3.43) and its salts and esters,ioxynil (N.3.44) and its salts and esters, bromacil (N.3.45), lenacil(N.3.46), terbacil (N.3.47), bentazon (N.3.48), bentazon-sodium(N.3.49), pyridate (N.3.50), pyridafol (N.3.51), pentanochlor (N.3.52),propanil (N.3.53); diquat (N.3.54), diquat-dibromide (N.3.55), paraquat(N.3.56), paraquat-dichloride (N.3.57), paraquat-dimetilsulfate(N.3.58);

N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen (N.4.1),acifluorfen-sodium (N.4.2), azafenidin (N.4.3), bencarbazone (N.4.4),benzfendizone (N.4.5), bifenox (N.4.6), butafenacil (N.4.7),carfentrazone (N.4.8), carfentrazone-ethyl (N.4.9), chlormethoxyfen(N.4.10), cinidon-ethyl (N.4.11), fluazolate (N.4.12), flufenpyr(N.4.13), flufenpyr-ethyl (N.4.14), flumiclorac (N.4.15),flumiclorac-pentyl (N.4.16), flumioxazin (N.4.17), fluoroglycofen(N.4.18), fluoroglycofen-ethyl (N.4.19), fluthiacet (N.4.20),fluthiacet-methyl (N.4.21), fomesafen (N.4.22), halosafen (N.4.23),lactofen (N.4.24), oxadiargyl (N.4.25), oxadiazon (N.4.26), oxyfluorfen(N.4.27), pentoxazone (N.4.28), profluazol (N.4.29), pyraclonil(N.4.30), pyraflufen (N.4.31), pyraflufen-ethyl (N.4.32), saflufenacil(N.4.33), sulfentrazone (N.4.34), thidiazimin (N.4.35), tiafenacil(N.4.36), trifludimoxazin (N.4.37), ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate((N.4.38) CAS 353292-31-6),N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide((N.4.39) CAS 452098-92-9), Ntetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide((N.4.40) CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyl¬phenoxy)-5-methyl-1H-pyrazole-1-carboxamide((N.4.41) CAS 452099-05-7), Ntetrahydro¬furfuryl-3-(2-chloro-6-fluoro-4-trifluoro¬methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide((N.4.42) CAS 452100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione((N.4.43) CAS 451484-50-7),2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione((N.4.44) CAS 1300118-96-0),1-methyl-6-trifluoro¬methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione((N.4.45) CAS 1304113-05-0), methyl(E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate((N.4.46) CAS 948893-00-3),3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione((N.4.47) CAS 212754-02-4);

N.5 Bleacher herbicides: beflubutamid (N.5.1), diflufenican (N.5.2),fluridone (N.5.3), flurochloridone (N.5.4), flurtamone (N.5.5),norflurazon (N.5.6), picolinafen (N.5.7),4-(3-trifluoromethyl¬phenoxy)-2-(4-trifluoromethylphenyl)¬pyrimidine((N.5.8) CAS 180608-33-7); benzobicyclon (N.5.9), benzofenap (N.5.10),bicyclopyrone (N.5.11), clomazone (N.5.12), fenquintrione (N.5.13),isoxaflutole (N.5.14), mesotrione (N.5.15), pyrasulfotole (N.5.16),pyrazolynate (N.5.17), pyrazoxyfen (N.5.18), sulcotrione (N.5.19),tefuryltrione (N.5.20), tembotrione (N.5.21), tolpyralate (N.5.22),topramezone (N.5.23); aclonifen (N.5.24), amitrole (N.5.25), flumeturon(N.5.26);

N.6 EPSP synthase inhibitors: glyphosate (N.6.1),glyphosate-isopropylammonium (N.6.2), glyposate-potassium (N.6.3),glyphosate-trimesium (sulfosate) (N.6.4);

N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos) (N.7.1),bilanaphos-sodium (N.7.2), glufosinate (N.7.3), glufosinate-P (N.7.4),glufosinate-ammonium (N.7.5);

N.8 DHP synthase inhibitors: asulam (N.8.1);

N.9 Mitosis inhibitors: benfluralin (N.9.1), butralin (N.9.2),dinitramine (N.9.3), ethalfluralin (N.9.4), fluchloralin (N.9.5),oryzalin (N.9.6), pendimethalin (N.9.7), prodiamine (N.9.8), trifluralin(N.9.9); amiprophos (N.9.10), amiprophos-methyl (N.9.11), butamiphos(N.9.12); chlorthal (N.9.13), chlorthal-dimethyl (N.9.14), dithiopyr(N.9.15), thiazopyr (N.9.16), propyzamide (N.9.17), tebutam (N.9.18);carbetamide (N.9.19), chlorpropham (N.9.20), flamprop (N.9.21),flamprop-isopropyl (N.9.22), flamprop-methyl (N.9.23),flamprop-M-isopropyl (N.9.24), flamprop-M-methyl (N.9.25), propham(N.9.26);

N.10 VLCFA inhibitors: acetochlor (N.10.1), alachlor (N.10.2), butachlor(N.10.3), dimethachlor (N.10.4), dimethenamid (N.10.5), dimethenamid-P(N.10.6), metazachlor (N.10.7), metolachlor (N.10.8), metolachlor-S(N.10.9), pethoxamid (N.10.10), pretilachlor (N.10.11), propachlor(N.10.12), propisochlor (N.10.13), thenylchlor (N.10.14), flufenacet(N.10.15), mefenacet (N.10.16), diphenamid (N.10.17), naproanilide(N.10.18), napropamide (N.10.19), napropamide-M (N.10.20), fentrazamide(N.10.21), anilofos (N.10.22), cafenstrole (N.10.23), fenoxasulfone(N.10.24), ipfencarbazone (N.10.25), piperophos (N.10.26), pyroxasulfone(N.10.27), isoxazoline compounds of the formulae II.1, II.2, II.3, II.4,II.5, II.6, II.7, II.8 and II.9

N.11 Cellulose biosynthesis inhibitors: chlorthiamid (N.11.1),dichlobenil (N.11.2), flupoxam (N.11.3), indaziflam (N.11.4), isoxaben(N.11.5), triaziflam (N.11.6),1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine((N.11.7) CAS 175899-01-1);

N.12 Decoupler herbicides: dinoseb (N.12.1), dinoterb (N.12.2), DNOC(N.12.3) and its salts;

N.13 Auxinic herbicides: 2,4-D (N.13.1) and its salts and esters,clacyfos (N.13.2), 2,4-DB (N.13.3) and its salts and esters,aminocyclopyrachlor (N.13.4) and its salts and esters, aminopyralid(N.13.5) and its salts such as aminopyralid-dimethylammonium (N.13.6),aminopyralid-tris(2-hydroxypropyl)ammonium (N.13.7) and its esters,benazolin (N.13.8), benazolin-ethyl (N.13.9), chloramben (N.13.10) andits salts and esters, clomeprop (N.13.11), clopyralid (N.13.12) and itssalts and esters, dicamba (N.13.13) and its salts and esters,dichlorprop (N.13.14) and its salts and esters, dichlorprop-P (N.13.15)and its salts and esters, fluroxypyr (N.13.16), fluroxypyr-butometyl(N.13.17), fluroxypyr-meptyl (N.13.18), halauxifen (N.13.) and its saltsand esters (CAS 943832-60-8); MCPA (N.13.) and its salts and esters,MCPA-thioethyl (N.13.19), MCPB (N.13.20) and its salts and esters,mecoprop (N.13.21) and its salts and esters, mecoprop-P (N.13.22) andits salts and esters, picloram (N.13.23) and its salts and esters,quinclorac (N.13.24), quinmerac (N.13.25), TBA (2,3,6) (N.13.26) and itssalts and esters, triclopyr (N.13.27) and its salts and esters,4-amino-3-chloro-6-(4-chloro-2-fluoro-3-meth-oxyphenyl)-5-fluoropyridine-2-carboxylicacid (N.13.28), benzyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate((N.13.29) CAS 1390661-72-9);

N.14 Auxin transport inhibitors: diflufenzopyr (N.14.1),diflufenzopyr-sodium (N.14.2), naptalam (N.14.3) and naptalam-sodium(N.14.4);

N.15 Other herbicides: bromobutide (N.15.1), chlorflurenol (N.15.2),chlorflurenol-methyl (N.15.3), cinmethylin (N.15.4), cumyluron (N.15.5),cyclopyrimorate ((N.15.6) CAS 499223-49-3) and its salts and esters,dalapon (N.15.7), dazomet (N.15.8), difenzoquat (N.15.9),difenzoquat-metilsulfate (N.15.10), dimethipin (N.15.11), DSMA(N.15.12), dymron (N.15.13), endothal (N.15.14) and its salts,etobenzanid (N.15.15), flurenol (N.15.16), flurenol-butyl (N.15.17),flurprimidol (N.15.18), fosamine (N.15.19), fosamine-ammonium (N.15.20),indanofan (N.15.21), maleic hydrazide (N.15.22), mefluidide (N.15.23),metam (N.15.24), methiozolin ((N.15.25) CAS 403640-27-7), methyl azide(N.15.26), methyl bromide (N.15.27), methyl-dymron (N.15.28), methyliodide (N.15.29), MSMA (N.15.30), oleic acid (N.15.31), oxaziclomefone(N.15.32), pelargonic acid (N.15.33), pyributicarb (N.15.34),quinoclamine (N.15.35), tridiphane (N.15.36);

O) Insecticides from classes O.1 to O.29

O.1 Acetylcholine esterase (AChE) inhibitors: aldicarb (O.1.1),alanycarb (O.1.2), bendiocarb (O.1.3), benfuracarb (O.1.4), butocarboxim(O.1.5), butoxycarboxim (O.1.6), carbaryl (O.1.7), carbofuran (O.1.8),carbosulfan (O.1.9), ethiofencarb (O.1.10), fenobucarb (O.1.11),formetanate (O.1.12), furathiocarb (O.1.13), isoprocarb (O.1.14),methiocarb (O.1.15), methomyl (O.1.16), metolcarb (O.1.17), oxamyl(O.1.18), pirimicarb (O.1.19), propoxur (O.1.20), thiodicarb (O.1.21),thiofanox (O.1.22), trimethacarb (O.1.23), XMC (O.1.24), xylylcarb(O.1.25) and triazamate (O.1.26); acephate (O.1.27), azamethiphos(O.1.28), azinphos-ethyl (O.1.29), azinphosmethyl (O.1.30), cadusafos(O.1.31), chlorethoxyfos (O.1.32), chlorfenvinphos (O.1.33), chlormephos(O.1.34), chlorpyrifos (O.1.35), chlorpyrifos-methyl (O.1.36), coumaphos(O.1.37), cyanophos (O.1.38), demeton-S-methyl (O.1.39), diazinon(O.1.40), dichlorvos/DDVP (O.1.41), dicrotophos (O.1.42), dimethoate(O.1.43), dimethylvinphos (O.1.44), disulfoton (O.1.45), EPN (O.1.46),ethion (O.1.47), ethoprophos (O.1.48), famphur (O.1.49), fenamiphos(O.1.50), fenitrothion (O.1.51), fenthion (O.1.52), fosthiazate(O.1.53), heptenophos (O.1.54), imicyafos (O.1.55), isofenphos (O.1.56),isopropyl 0-(methoxyaminothio-phosphoryl) salicylate (O.1.57),isoxathion (O.1.58), malathion (O.1.59), mecarbam (O.1.60),methamidophos (O.1.61), methidathion (O.1.62), mevinphos (O.1.63),monocrotophos (O.1.64), naled (O.1.65), omethoate (O.1.66),oxydemeton-methyl (O.1.67), parathion (O.1.68), parathion-methyl(O.1.69), phenthoate (O.1.70), phorate (O.1.71), phosalone (O.1.72),phosmet (O.1.73), phosphamidon (O.1.74), phoxim (O.1.75),pirimiphos-methyl (O.1.76), profenofos (O.1.77), propetamphos (O.1.78),prothiofos (O.1.79), pyraclofos (O.1.80), pyridaphenthion (O.1.81),quinalphos (O.1.82), sulfotep (O.1.83), tebupirimfos (O.1.84), temephos(O.1.85), terbufos (O.1.86), tetrachlorvinphos (O.1.87), thiometon(O.1.88), triazophos (O.1.89), trichlorfon (O.1.90), vamidothion(O.1.91);

O.2 GABA-gated chloride channel antagonists: endosulfan (O.2.1),chlordane (O.2.2); ethiprole (O.2.3), fipronil (O.2.4), flufiprole(O.2.5), pyrafluprole (O.2.6), pyriprole (O.2.7);

O.3 Sodium channel modulators: acrinathrin (O.3.1), allethrin (O.3.2),d-cis-trans allethrin (O.3.3), d-trans allethrin (O.3.4), bifenthrin(O.3.5), bioallethrin (O.3.6), bioallethrin S-cylclopentenyl (O.3.7),bioresmethrin (O.3.8), cycloprothrin (O.3.9), cyfluthrin (O.3.10),beta-cyfluthrin (O.3.11), cyhalothrin (O.3.12), lambda-cyhalothrin(O.3.13), gamma-cyhalothrin (O.3.14), cypermethrin (O.3.15),alpha-cypermethrin (O.3.16), beta-cypermethrin (O.3.17),theta-cypermethrin (O.3.18), zeta-cypermethrin (O.3.19), cyphenothrin(O.3.20), deltamethrin (O.3.21), empenthrin (O.3.22), esfenvalerate(O.3.23), etofenprox (O.3.24), fenpropathrin (O.3.25), fenvalerate(O.3.26), flucythrinate (O.3.27), flumethrin (O.3.28), tau-fluvalinate(O.3.29), halfenprox (O.3.30), heptafluthrin (O.3.31), imiprothrin(O.3.32), meperfluthrin (O.3.33), metofluthrin (O.3.34), momfluorothrin(O.3.35), permethrin (O.3.36), phenothrin (O.3.37), prallethrin(O.3.38), profluthrin (O.3.39), pyrethrin (pyrethrum) (O.3.40),resmethrin (O.3.41), silafluofen (O.3.42), tefluthrin (O.3.43),tetramethylfluthrin (O.3.44), tetramethrin (O.3.45), tralomethrin(O.3.46) and transfluthrin (O.3.47); DDT (O.3.48), methoxychlor(O.3.49);

O.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid(O.4.1), clothianidin (O.4.2), cycloxaprid (O.4.3), dinotefuran (O.4.4),imidacloprid (O.4.5), nitenpyram (O.4.6), thiacloprid (O.4.7),thiamethoxam (O.4.8);(2E)-1-[(6-chloropyridin-3-Amethyl]-N′-nitro-2-pentylidene-hydrazinecarboximidamide(O.4.9);1-[(6-chloropyridin-3-Amethyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine(O.4.10); nicotine (O.4.11);

O.5 Nicotinic acetylcholine receptor allosteric activators: spinosad(O.5.1), spinetoram (O.5.2);

O.6 Chloride channel activators: abamectin (O.6.1), emamectin benzoate(O.6.2), ivermectin (O.6.3), lepimectin (O.6.4), milbemectin (O.6.5);

O.7 Juvenile hormone mimics: hydroprene (O.7.1), kinoprene (O.7.2),methoprene (O.7.3); fenoxycarb (O.7.4), pyriproxyfen (O.7.5);

O.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide(O.8.1) and other alkyl halides; chloropicrin (O.8.2), sulfuryl fluoride(O.8.3), borax (O.8.4), tartar emetic (O.8.5);

O.9 Selective homopteran feeding blockers: pymetrozine (O.9.1),flonicamid (O.9.2);

O.10 Mite growth inhibitors: clofentezine (O.10.1), hexythiazox(O.10.2), diflovidazin (O.10.3); etoxazole (O.10.4);

O.11 Microbial disruptors of insect midgut membranes: the Bt cropproteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,Cry34/35Ab1;

O.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron (O.12.1);azocyclotin (O.12.2), cyhexatin (O.12.3), fenbutatin oxide (O.12.4),propargite (O.12.5), tetradifon (O.12.6);

O.13 Uncouplers of oxidative phosphorylation via disruption of theproton gradient: chlorfenapyr (O.13.1), DNOC (O.13.2), sulfluramid(O.13.3);

O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers:bensultap (O.14.1), cartap hydrochloride (O.14.2), thiocyclam (O.14.3),thiosultap sodium (O.14.4);

O.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron(O.15.1), chlorfluazuron (O.15.2), diflubenzuron (O.15.3), flucycloxuron(O.15.4), flufenoxuron (O.15.5), hexaflumuron (O.15.6), lufenuron(O.15.7), novaluron (O.15.8), noviflumuron (O.15.9), teflubenzuron(O.15.10), triflumuron (O.15.11);

O.16 Inhibitors of the chitin biosynthesis type 1: buprofezin (O.16.1);

O.17 Moulting disruptors: cyromazine (O.17.1);

O.18 Ecdyson receptor agonists: methoxyfenozide (O.18.1), tebufenozide(O.18.2), halofenozide (O.18.3), fufenozide (O.18.4), chromafenozide(O.18.5);

O.19 Octopamin receptor agonists: amitraz (O.19.1);

O.20 Mitochondrial complex III electron transport inhibitors:hydramethylnon (O.20.1), acequinocyl (O.20.2), fluacrypyrim (O.20.3);

O.21 Mitochondrial complex I electron transport inhibitors: fenazaquin(O.21.1), fenpyroximate (O.21.2), pyrimidifen (O.21.3), pyridaben(O.21.4), tebufenpyrad (O.21.5), tolfenpyrad (O.21.6); rotenone(O.21.7);

O.22 Voltage-dependent sodium channel blockers: indoxacarb (O.22.1),metaflumizone (O.22.2),2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N4-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide(O.22.3),N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide(O.22.4);

O.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen(O.23.1), spiromesifen (O.23.2), spirotetramat (O.23.3);

O.24 Mitochondrial complex IV electron transport inhibitors: aluminiumphosphide (O.24.1), calcium phosphide (O.24.2), phosphine (O.24.3), zincphosphide (O.24.4), cyanide (O.24.5);

O.25 Mitochondrial complex II electron transport inhibitors:cyenopyrafen (O.25.1), cyflumetofen (O.25.2);

O.26 Ryanodine receptor-modulators: flubendiamide (O.26.1),chlorantraniliprole (O.26.2), cyantraniliprole (O.26.3), cyclaniliprole(O.26.4), tetraniliprole (O.26.5);(R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethypethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide(O.26.6),(S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethypethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide(O.26.7),methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate(O.26.8);N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)-carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide(O.26.9);N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide(O.26.10);N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide(O.26.11);N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide(O.26.12);N-[4,6-di-bromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(tri-fluoromethyl)pyrazole-3-carboxamide(O.26.13);N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(O.26.14);3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide(O.26.15);3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide(O.26.16);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(O.26.17); cyhalodiamide (O.26.18);

O.27. insecticidal active compounds of unknown or uncertain mode ofaction: afidopyropen (O.27.1), afoxolaner (O.27.2), azadirachtin(O.27.3), amidoflumet (O.27.4), benzoximate (O.27.5), bifenazate(O.27.6), broflanilide (O.27.7), bromopropylate (O.27.8), chinomethionat(O.27.9), cryolite (O.27.10), dicloromezotiaz (O.27.11), dicofol(O.27.12), flufenerim (O.27.13), flometoquin (O.27.14), fluensulfone(O.27.15), fluhexafon (O.27.16), fluopyram (O.27.17), flupyradifurone(O.27.18), fluralaner (O.27.19), metoxadiazone (O.27.20), piperonylbutoxide (O.27.21), pyflubumide (O.27.22), pyridalyl (O.27.23),pyrifluquinazon (O.27.24), sulfoxaflor (O.27.25), tioxazafen (O.27.26),triflumezopyrim (O.27.27),11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one(O.27.28),3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one(O.27.28),1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(O.27.29),(E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide(O.27.31);(E/Z)—N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide(O.27.32);(E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide(O.27.33);(E/Z)—N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide(O.27.34);(E/Z)—N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide(O.27.35);(E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide(O.27.36);(E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide(O.27.37);(E/Z)—N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide(O.27.38);(E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide(O.27.39);N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide(O.27.40);N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N′-isopropyl-acetamidine(O.27.41); fluazaindolizine (O.27.42);4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide(O.27.43); fluxamet-amide (O.27.44);5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole(O.27.45);3-(benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyppropyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide(O.27.46);3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethypethyl]-6-(trifluoromethyl)phenyl]-benzamide(O.27.47);N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyhethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide(O.27.48);N-[3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyhethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide(O.27.49);4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyhethyl]-6-(trifluoro-methyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide(O.27.50);3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethypethyl]-6(trifluoromethyl)phenyl]amino]-carbonyl]phenyl]-N-methyl-benzamide(O.27.51);2-chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethypethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide(O.27.52);4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluorometh-yl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide(O.27.53);4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]-2-fluoro-benzamide(O.27.54);N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide(O.27.55);N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyhethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide(O.27.56);N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide(O.27.57);4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-carbamoyl]phenyl]-2-methyl-benzamide(O.27.58);4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyhethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide(O.27.59);N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide(O.27.60); 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine;2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine(O.27.61); 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine(O.27.62);N-methylsulfonyl-6-[2-(3-pyridyhthiazol-5-yl]pyridine-2-carboxamide(O.27.63);N-methylsulfonyl-6-[2-(3-pyridyhthiazol-5-yl]pyridine-2-carboxamide(O.27.64);N-ethyl-N-[4-methyl-2-(3-pyridyhthiazol-5-yl]-3-methylthio-propanamide(O.27.65);N-methyl-N-[4-methyl-2-(3-pyridyhthiazol-5-yl]-3-methylthio-propanamide(O.27.66);N,2-dimethyl-N-[4-methyl-2-(3-pyridyhthiazol-5-yl]-3-methylthio-propanamide(O.27.67);N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide(O.27.68);N-[4-chloro-2-(3-pyridyhthiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide(O.2769.);N-[4-chloro-2-(3-pyridyhthiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide(O.27.70);N-[4-chloro-2-(3-pyridyhthiazol-5-yl]-N-methyl-3-methylthio-propanamide(O.27.71);N-[4-chloro-2-(3-pyridyhthiazol-5-yl]-N-ethyl-3-methylthio-propanamide(O.27.72);1-[(6-chloro-3-pyri-dinyhmethyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine(O.27.73);1-[(6-chloropyridin-3-yhmethyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol(O.27.74);1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.75);1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.76);N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide(O.27.77);1-[1-(1-cyanocyclopropypethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.78);N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.79);1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.80);1-[1-(1-cyanocyclopropypethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.81);N-methyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.82);1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.83);1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.84), N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide(O.27.85); N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide(O.27.86); N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide(O.27.87);2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide(O.27.88);2-(3-pyridinyl)-N-[(tetrahydro-2-furanyhmethyl]-2H-indazole-5-carboxamide(O.27.89); methyl2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate(O.27.90);N-[(2,2-difluorocyclopropyhmethyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide(O.27.91);N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide(O.27.92);2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide(O.27.93);N-[(5-methyl-2-pyrazinyhmethyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide(O.27.94),N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)-propanamide(O.27.95);N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide(O.27.96);N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-di-fluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide(O.27.97);N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyhmethylsulfinyl]-N-ethyl-propanamide(O.27.98); sarolaner (O.27.99), lotilaner (O.27.100).

The active substances referred to as component 2, their preparation andtheir activity e. g. against harmful fungi is known (cf.:http://www.alanwood.net/pesticides/); these substances are commerciallyavailable. The compounds described by IUPAC nomenclature, theirpreparation and their pesticidal activity are also known (cf. Can. J.Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE19650197; DE 10021412; DE 102005009458; U.S. Pat. Nos. 3,296,272;3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO06/87343; WO 07/82098; WO 07/90624, WO 10/139271, WO 11/028657, WO12/168188, WO 07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO13/127704, WO 13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO13/092224, WO 11/135833, CN 1907024, CN 1456054, CN 103387541, CN1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO13/116251, WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO07/129454, WO 12/165511, WO 11/081174, WO 13/47441).

The present invention furthermore relates to agrochemical compositionscomprising a mixture of at least one compound I (component 1) and atleast one further active substance useful for plant protection, e. g.selected from the groups A) to O) (component 2), in particular onefurther fungicide, e. g. one or more fungicide from the groups A) to K),as described above, and if desired one suitable solvent or solidcarrier. Those mixtures are of particular interest, since many of themat the same application rate show higher efficiencies against harmfulfungi. Furthermore, combating harmful fungi with a mixture of compoundsI and at least one fungicide from groups A) to K), as described above,is more efficient than combating those fungi with individual compounds Ior individual fungicides from groups A) to K).

By applying compounds I together with at least one active substance fromgroups A) to O) a synergistic effect can be obtained, i.e. more thensimple addition of the individual effects is obtained (synergisticmixtures).

This can be obtained by applying the compounds I and at least onefurther active substance simultaneously, either jointly (e. g. astank-mix) or seperately, or in succession, wherein the time intervalbetween the individual applications is selected to ensure that theactive substance applied first still occurs at the site of action in asufficient amount at the time of application of the further activesubstance(s). The order of application is not essential for working ofthe present invention.

When applying compound I and a pesticide II sequentially the timebetween both applications may vary e. g. between 2 hours to 7 days. Alsoa broader range is possible ranging from 0.25 hour to 30 days,preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 daysor from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.

In the binary mixtures and compositions according to the invention theweight ratio of the component 1) and the component 2) generally dependsfrom the properties of the active components used, usually it is in therange of from 1:10,000 to 10,000:1, often it is in the range of from1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferablyin the range of from 1:20 to 20:1, more preferably in the range of from1:10 to 10:1, even more preferably in the range of from 1:4 to 4:1 andin particular in the range of from 1:2 to 2:1.

According to further embodiments of the binary mixtures andcompositions, the weight ratio of the component 1) and the component 2)usually is in the range of from 1000:1 to 1:1, often in the range offrom 100:1 to 1:1, regularly in the range of from 50:1 to 1:1,preferably in the range of from 20:1 to 1:1, more preferably in therange of from 10:1 to 1:1, even more preferably in the range of from 4:1to 1:1 and in particular in the range of from 2:1 to 1:1.

According to a further embodiments of the binary mixtures andcompositions, the weight ratio of the component 1) and the component 2)usually is in the range of from 1:1 to 1:1000, often in the range offrom 1:1 to 1:100, regularly in the range of from 1:1 to 1:50,preferably in the range of from 1:1 to 1:20, more preferably in therange of from 1:1 to 1:10, even more preferably in the range of from 1:1to 1:4 and in particular in the range of from 1:1 to 1:2.

In the ternary mixtures, i.e. compositions according to the inventioncomprising the component 1) and component 2) and a compound III(component 3), the weight ratio of component 1) and component 2) dependsfrom the properties of the active substances used, usually it is in therange of from 1:100 to 100:1, regularly in the range of from 1:50 to50:1, preferably in the range of from 1:20 to 20:1, more preferably inthe range of from 1:10 to 10:1 and in particular in the range of from1:4 to 4:1, and the weight ratio of component 1) and component 3)usually it is in the range of from 1:100 to 100:1, regularly in therange of from 1:50 to 50:1, preferably in the range of from 1:20 to20:1, more preferably in the range of from 1:10 to 10:1 and inparticular in the range of from 1:4 to 4:1.

Any further active components are, if desired, added in a ratio of from20:1 to 1:20 to the component 1).

These ratios are also suitable for inventive mixtures applied by seedtreatment.

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from inhibitors of complex III at Q_(o)site in group A), more preferably selected from compounds (A.1.1),(A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14),(A.1.17), (A.1.21), (A.1.24), (A.1.25), (A.1.26), (A.1.27), (A.1.30),(A.1.31), (A.1.32), (A.1.34) and (A.1.35); particularly selected from(A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17),(A.1.24), (A.1.25), (A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32),(A.1.34) and (A.1.35). Preference is also given to mixtures comprisingas component 2) at least one active substance selected from inhibitorsof complex III at Q_(i) site in group A), more preferably selected fromcompounds (A.2.1), (A.2.3) and (A.2.4); particularly selected from(A.2.3) and (A.2.4).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from inhibitors of complex II in group A),more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4),(A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17),(A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.24),(A.3.25), (A.3.27), (A.3.28), (A.3.29), (A.3.31), (A.3.32), (A.3.33),(A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39);particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9),(A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.24),(A.3.25), (A.3.27), (A.3.29), (A.3.31), (A.3.32), (A.3.33), (A.3.34),(A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from other respiration nhibitors in groupA), more preferably selected from compounds (A.4.5) and (A.4.11); inparticular (A.4.11).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from C14 demethylase inhibitors in groupB), more preferably selected from compounds (B.1.4), (B.1.5), (B.1.8),(B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21),(B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.34), (B.1.37),(B.1.38), (B.1.43) and (B.1.46); particularly selected from (B.1.5),(B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33),(B.1.34), (B.1.37), (B.138), (B.1.43) and (B.1.46).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from Delta14-reductase inhibitors in groupB), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6)and (B.2.8); in particular (B.2.4).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from phenylamides and acyl amino acidfungicides in group C), more preferably selected from compounds (C.1.1),(C.1.2), (C.1.4) and (C.1.5); particularly selected from (C.1.1) and(C.1.4).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from other nucleic acid synthesisinhibitors in group C), more preferably selected from compounds (C.2.6),(C.2.7) and (C.2.8).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group D), more preferably selectedfrom compounds (D.1.1), (D.1.2), (D.1.5), (D.2.4) and (D.2.6);particularly selected from (D.1.2), (D.1.5) and (D.2.6).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group E), more preferably selectedfrom compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); in particular(E.1.3).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group F), more preferably selectedfrom compounds (F.1.2), (F.1.4) and (F.1.5).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group G), more preferably selectedfrom compounds (G.3.1), (G.3.3), (G.3.6), (G.5.1), (G.5.2), (G.5.3),(G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and(G.5.11); particularly selected from (G.3.1), (G.5.1), (G.5.2) and(G.5.3).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group H), more preferably selectedfrom compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2),(H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from(H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group I), more preferably selectedfrom compounds (I.2.2) and (I.2.5).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group J), more preferably selectedfrom compounds (J.1.2), (J.1.5) and (J.1.8); in particular (J.1.5).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group K), more preferably selectedfrom compounds (K.1.41), (K.1.42), (K.1.44), (K.1.45), (K.1.47) and(K.1.49); particularly selected from (K.1.41), (K.1.44), (K.1.45),(K.1.47) and (K.1.49).

Accordingly, the present invention furthermore relates to mixturescomprising one compound of the formula I (component 1) and one pesticideII (component 2), wherein pesticide II is selected from the column “Co.2” of the lines B-1 to B-727 of Table B.

A further embodiment relates to the mixtures B-1 to B-727 listed inTable B, where a row of Table B corresponds in each case to a fungicidalmixture comprising as active components one of the in the presentspecification individualized compounds of formula I, i.e. compoundsI.A.A-1 to I.A.A-503, I.B.A-1 to I.B.A-503, I.C.A-1 to I.C.A-503,I.D.A-1 to I.D.A-503, I.E.A-1 to I.E.A-503, I.F.A-1 to I.F.A-503,I.G.A-1 to I.G.A-503, I.H.A-1 to I.H.A-503, I.I.A-1 to I.I.A-503 andI.J.A-1 to I.J.A-503 as defined in tables 1 to 11 (component 1 in column“Co.1”) and the respective pesticide II from groups A) to O) (component2) stated in the row in question.

Another embodiment relates to the mixtures B-1 to B-727 listed in TableB, where a row of Table B corresponds in each case to a fungicidalmixture comprising as active components one of the compounds Ex-1 toEx-7 of formula I as defined below in table I (component 1 in column“Co.1”) and the respective pesticide 11 from groups A) to O) (component2) stated in the row in question.

Preferably, the compositions described in Table B comprise the activecomponents in synergistically effective amounts.

TABLE B Mixtures comprising as active components one indiviualizedcompound of the fomula I (in column Co. 1), and as component 2) (incolumn Co. 2) one pesticide from groups A) to O) [which is coded e.g. as(A.1.1) for azoxystrobin as defined above]. Mixt. Co. 1 Co. 2 B-1 (I)(A.1.1) B-2 (I) (A.1.2) B-3 (I) (A.1.3) B-4 (I) (A.1.4) B-5 (I) (A.1.5)B-6 (I) (A.1.6) B-7 (I) (A.1.7) B-8 (I) (A.1.8) B-9 (I) (A.1.9) B-10 (I)(A.1.10) B-11 (I) (A.1.11) B-12 (I) (A.1.12) B-13 (I) (A.1.13) B-14 (I)(A.1.14) B-15 (I) (A.1.15) B-16 (I) (A.1.16) B-17 (I) (A.1.17) B-18 (I)(A.1.18) B-19 (I) (A.1.19) B-20 (I) (A.1.20) B-21 (I) (A.1.21) B-22 (I)(A.1.22) B-23 (I) (A.1.23) B-24 (I) (A.1.24) B-25 (I) (A.1.25) B-26 (I)(A.1.26) B-27 (I) (A.1.27) B-28 (I) (A.1.30) B-29 (I) (A.1.31) B-30 (I)(A.1.32) B-31 (I) (A.2.1) B-32 (I) (A.2.2) B-33 (I) (A.2.3) B-34 (I)(A.2.4) B-35 (I) (A.2.6) B-36 (I) (A.2.7) B-37 (I) (A.2.8) B-38 (I)(A.3.1) B-39 (I) (A.3.2) B-40 (I) (A.3.3) B-41 (I) (A.3.4) B-42 (I)(A.3.5) B-43 (I) (A.3.6) B-44 (I) (A.3.7) B-45 (I) (A.3.8) B-46 (I)(A.3.9) B-47 (I) (A.3.10) B-48 (I) (A.3.11) B-49 (I) (A.3.12) B-50 (I)(A.3.13) B-51 (I) (A.3.14) B-52 (I) (A.3.15) B-53 (I) (A.3.16) B-54 (I)(A.3.17) B-55 (I) (A.3.18) B-56 (I) (A.3.19) B-57 (I) (A.3.20) B-58 (I)(A.3.21) B-59 (I) (A.3.22) B-60 (I) (A.3.23) B-61 (I) (A.3.24) B-62 (I)(A.3.25) B-63 (I) (A.3.26) B-64 (I) (A.3.27) B-65 (I) (A.3.28) B-66 (I)(A.3.29) B-67 (I) (A.3.30) B-68 (I) (A.3.31) B-69 (I) (A.3.32) B-70 (I)(A.3.33) B-71 (I) (A.3.34) B-72 (I) (A.3.35) B-73 (I) (A.3.36) B-74 (I)(A.3.37) B-75 (I) (A.3.38) B-76 (I) (A.3.39) B-77 (I) (A.4.1) B-78 (I)(A.4.2) B-79 (I) (A.4.3) B-80 (I) (A.4.4) B-81 (I) (A.4.5) B-82 (I)(A.4.6) B-83 (I) (A.4.7) B-84 (I) (A.4.8) B-85 (I) (A.4.9) B-86 (I)(A.4.10) B-87 (I) (A.4.11) B-88 (I) (A.4.12) B-89 (I) (B.1.1) B-90 (I)(B.1.2) B-91 (I) (B.1.3) B-92 (I) (B.1.4) B-93 (I) (B.1.5) B-94 (I)(B.1.6) B-95 (I) (B.1.7) B-96 (I) (B.1.8) B-97 (I) (B.1.9) B-98 (I)(B.1.10) B-99 (I) (B.1.11) B-100 (I) (B.1.12) B-101 (I) (B.1.13) B-102(I) (B.1.14) B-103 (I) (B.1.15) B-104 (I) (B.1.16) B-105 (I) (B.1.17)B-106 (I) (B.1.18) B-107 (I) (B.1.19) B-108 (I) (B.1.20) B-109 (I)(B.1.21) B-110 (I) (B.1.22) B-111 (I) (B.1.23) B-112 (I) (B.1.24) B-113(I) (B.1.25) B-114 (I) (B.1.26) B-115 (I) (B.1.27) B-116 (I) (B.1.28)B-117 (I) (B.1.29) B-118 (I) (B.1.30) B-119 (I) (B.1.34) B-120 (I)(B.1.37) B-121 (I) (B.1.38) B-122 (I) (B.1.43) B-123 (I) (B.1.44) B-124(I) (B.1.45) B-125 (I) (B.1.46) B-126 (I) (B.1.47) B-127 (I) (B.1.48)B-128 (I) (B.1.49) B-129 (I) (B.1.50) B-130 (I) (B.1.51) B-131 (I)(B.2.1) B-132 (I) (B.2.2) B-133 (I) (B.2.3) B-134 (I) (B.2.4) B-135 (I)(B.2.5) B-136 (I) (B.2.6) B-137 (I) (B.2.7) B-138 (I) (B.2.8) B-139 (I)(B.3.1) B-140 (I) (C.1.1) B-141 (I) (C.1.2) B-142 (I) (C.1.3) B-143 (I)(C.1.4) B-144 (I) (C.1.5) B-145 (I) (C.1.6) B-146 (I) (C.1.7) B-147 (I)(C.2.1) B-148 (I) (C.2.2) B-149 (I) (C.2.3) B-150 (I) (C.2.4) B-151 (I)(C.2.5) B-152 (I) (C.2.6) B-153 (I) (C.2.7) B-154 (I) (D.1.1) B-155 (I)(D.1.2) B-156 (I) (D.1.3) B-157 (I) (D.1.4) B-158 (I) (D.1.5) B-159 (I)(D.1.6) B-160 (I) (D.2.1) B-161 (I) (D.2.2) B-162 (I) (D.2.3) B-163 (I)(D.2.4) B-164 (I) (D.2.5) B-165 (I) (D.2.6) B-166 (I) (D.2.7) B-167 (I)(E.1.1) B-168 (I) (E.1.2) B-169 (I) (E.1.3) B-170 (I) (E.2.1) B-171 (I)(E.2.2) B-172 (I) (E.2.3) B-173 (I) (E.2.4) B-174 (I) (E.2.5) B-175 (I)(E.2.6) B-176 (I) (E.2.7) B-177 (I) (E.2.8) B-178 (I) (F.1.1) B-179 (I)(F.1.2) B-180 (I) (F.1.3) B-181 (I) (F.1.4) B-182 (I) (F.1.5) B-183 (I)(F.1.6) B-184 (I) (F.2.1) B-185 (I) (G.1.1) B-186 (I) (G.1.2) B-187 (I)(G.1.3) B-188 (I) (G.1.4) B-189 (I) (G.2.1) B-190 (I) (G.2.2) B-191 (I)(G.2.3) B-192 (I) (G.2.4) B-193 (I) (G.2.5) B-194 (I) (G.2.6) B-195 (I)(G.2.7) B-196 (I) (G.3.1) B-197 (I) (G.3.2) B-198 (I) (G.3.3) B-199 (I)(G.3.4) B-200 (I) (G.3.5) B-201 (I) (G.3.6) B-202 (I) (G.3.7) B-203 (I)(G.3.8) B-204 (I) (G.4.1) B-205 (I) (G.5.1) B-206 (I) (G.5.2) B-207 (I)(G.5.3) B-208 (I) (H.1.1) B-209 (I) (H.1.2) B-210 (I) (H.1.3) B-211 (I)(H.1.4) B-212 (I) (H.1.5) B-213 (I) (H.1.6) B-214 (I) (H.2.1) B-215 (I)(H.2.2) B-216 (I) (H.2.3) B-217 (I) (H.2.4) B-218 (I) (H.2.5) B-219 (I)(H.2.6) B-220 (I) (H.2.7) B-221 (I) (H.2.8) B-222 (I) (H.2.9) B-223 (I)(H.3.1) B-224 (I) (H.3.2) B-225 (I) (H.3.3) B-226 (I) (H.3.4) B-227 (I)(H.3.5) B-228 (I) (H.3.6) B-229 (I) (H.3.7) B-230 (I) (H.3.8) B-231 (I)(H.3.9) B-232 (I) (H.3.10) B-233 (I) (H.3.11) B-234 (I) (H.4.1) B-235(I) (H.4.2) B-236 (I) (H.4.3) B-237 (I) (H.4.4) B-238 (I) (H.4.5) B-239(I) (H.4.6) B-240 (I) (H.4.7) B-241 (I) (H.4.8) B-242 (I) (H.4.9) B-243(I) (H.4.10) B-244 (I) (I.1.1) B-245 (I) (I.1.2) B-246 (I) (I.2.1) B-247(I) (I.2.2) B-248 (I) (I.2.3) B-249 (I) (I.2.4) B-250 (I) (I.2.5) B-251(I) (J.1.1) B-252 (I) (J.1.2) B-253 (I) (J.1.3) B-254 (I) (J.1.4) B-255(I) (J.1.5) B-256 (I) (J.1.6) B-257 (I) (J.1.7) B-258 (I) (J.1.8) B-259(I) (J.1.9) B-260 (I) (J.1.10) B-261 (I) (K.1.1) B-262 (I) (K.1.2) B-263(I) (K.1.3) B-264 (I) (K.1.4) B-265 (I) (K.1.5) B-266 (I) (K.1.6) B-267(I) (K.1.7) B-268 (I) (K.1.8) B-269 (I) (K.1.9) B-270 (I) (K.1.10) B-271(I) (K.1.11) B-272 (I) (K.1.12) B-273 (I) (K.1.13) B-274 (I) (K.1.14)B-275 (I) (K.1.15) B-276 (I) (K.1.16) B-277 (I) (K.1.17) B-278 (I)(K.1.18) B-279 (I) (K.1.19) B-280 (I) (K.1.20) B-281 (I) (K.1.21) B-282(I) (K.1.22) B-283 (I) (K.1.23) B-284 (I) (K.1.24) B-285 (I) (K.1.25)B-286 (I) (K.1.26) B-287 (I) (K.1.27) B-288 (I) (K.1.28) B-289 (I)(K.1.29) B-290 (I) (K.1.30) B-291 (I) (K.1.31) B-292 (I) (K.1.32) B-293(I) (K.1.33) B-294 (I) (K.1.34) B-295 (I) (K.1.35) B-296 (I) (K.1.36)B-297 (I) (K.1.37) B-298 (I) (K.1.38) B-299 (I) (K.1.39) B-300 (I)(K.1.40) B-301 (I) (K.1.41) B-302 (I) (K.1.42) B-303 (I) (K.1.43) B-304(I) (K.1.44) B-305 (I) (K.1.45) B-306 (I) (K.1.47) B-307 (I) (M.1.1)B-308 (I) (M.1.2) B-309 (I) (M.1.3) B-310 (I) (M.1.4) B-311 (I) (M.1.5)B-312 (I) (M.1.6) B-313 (I) (M.1.7) B-314 (I) (M.1.8) B-315 (I) (M.1.9)B-316 (I) (M.1.10) B-317 (I) (M.1.11) B-318 (I) (M.1.12) B-319 (I)(M.1.13) B-320 (I) (M.1.14) B-321 (I) (M.1.15) B-322 (I) (M.1.16) B-323(I) (M.1.17) B-324 (I) (M.1.18) B-325 (I) (M.1.19) B-326 (I) (M.1.20)B-327 (I) (M.1.21) B-328 (I) (M.1.22) B-329 (I) (M.1.23) B-330 (I)(M.1.24) B-331 (I) (M.1.25) B-332 (I) (M.1.26) B-333 (I) (M.1.27) B-334(I) (M.1.28) B-335 (I) (M.1.29) B-336 (I) (M.1.30) B-337 (I) (M.1.31)B-338 (I) (M.1.32) B-339 (I) (M.1.33) B-340 (I) (M.1.34) B-341 (I)(M.1.35) B-342 (I) (M.1.36) B-343 (I) (M.1.37) B-344 (I) (M.1.38) B-345(I) (M.1.39) B-346 (I) (M.1.40) B-347 (I) (M.1.41) B-348 (I) (M.1.42)B-349 (I) (M.1.43) B-350 (I) (M.1.44) B-351 (I) (M.1.45) B-352 (I)(M.1.46) B-353 (I) (M.1.47) B-354 (I) (M.1.48) B-355 (I) (M.1.49) B-356(I) (M.1.50) B-357 (I) (N.1.1) B-358 (I) (N.1.2) B-359 (I) (N.1.3) B-360(I) (N.1.4) B-361 (I) (N.1.5) B-362 (I) (N.2.1) B-363 (I) (N.2.2) B-364(I) (N.2.3) B-365 (I) (N.3.1) B-366 (I) (N.3.2) B-367 (I) (N.3.3) B-368(I) (N.3.4) B-369 (I) (N.4.1) B-370 (I) (N.5.1) B-371 (I) (N.6.1) B-372(I) (N.6.2) B-373 (I) (N.6.3) B-374 (I) (N.6.4) B-375 (I) (N.6.5) B-376(I) (N.7.1) B-377 (I) (N.7.2) B-378 (I) (N.7.3) B-379 (I) (N.8.1) B-380(I) (N.9.1) B-381 (I) (N.10.1) B-382 (I) (N.10.2) B-383 (I) (N.10.3)B-384 (I) (N.10.4) B-385 (I) (N.10.5) B-386 (I) (N.11.1) B-387 (I)(N.12.1) B-388 (I) (N.12.2) B-389 (I) (N.12.3) B-390 (I) (N.12.4) B-391(I) (N.13.1) B-392 (I) (N.13.2) B-393 (I) (N.13.3) B-394 (I) (N.13.4)B-395 (I) (N.13.5) B-396 (I) (N.13.6) B-397 (I) (N.13.7) B-398 (I)(N.13.8) B-399 (I) (N.13.9) B-400 (I) (N.14.1) B-401 (I) (N.14.2) B-402(I) (N.14.3) B-403 (I) (N.15.1) B-404 (I) (N.16.1) B-405 (I) (N.16.2)B-406 (I) (N.17.1) B-407 (I) (N.17.2) B-408 (I) (N.17.3) B-409 (I)(N.17.4) B-410 (I) (N.17.5) B-411 (I) (N.17.6) B-412 (I) (N.17.7) B-413(I) (N.17.8) B-414 (I) (N.17.9) B-415 (I) (N.17.10) B-416 (I) (N.17.11)B-417 (I) (N.17.12) B-418 (I) (O.1.1) B-419 (I) (O.1.2) B-420 (I)(O.1.3) B-421 (I) (O.1.4) B-422 (I) (O.1.5) B-423 (I) (O.1.6) B-424 (I)(O.1.7) B-425 (I) (O.1.8) B-426 (I) (O.1.9) B-427 (I) (O.1.10) B-428 (I)(O.1.11) B-429 (I) (O.1.12) B-430 (I) (O.1.13) B-431 (I) (O.1.14) B-432(I) (O.1.15) B-433 (I) (O.1.16) B-434 (I) (O.1.17) B-435 (I) (O.1.18)B-436 (I) (O.1.19) B-437 (I) (O.1.20) B-438 (I) (O.1.21) B-439 (I)(O.1.22) B-440 (I) (O.1.23) B-441 (I) (O.1.24) B-442 (I) (O.1.25) B-443(I) (O.1.26) B-444 (I) (O.1.27) B-445 (I) (O.1.28) B-446 (I) (O.1.29)B-447 (I) (O.1.30) B-448 (I) (O.1.31) B-449 (I) (O.1.32) B-450 (I)(O.1.33) B-451 (I) (O.1.34) B-452 (I) (O.1.35) B-453 (I) (O.1.36) B-454(I) (O.1.37) B-455 (I) (O.1.38) B-456 (I) (O.2.1) B-457 (I) (O.2.2)B-458 (I) (O.2.3) B-459 (I) (O.2.4) B-460 (I) (O.2.5) B-461 (I) (O.2.6)B-462 (I) (O.2.7) B-463 (I) (O.2.8) B-464 (I) (O.2.9) B-465 (I) (O.2.10)B-466 (I) (O.2.11) B-467 (I) (O.2.12) B-468 (I) (O.2.13) B-469 (I)(O.2.14) B-470 (I) (O.2.15) B-471 (I) (O.2.16) B-472 (I) (O.3.1) B-473(I) (O.3.2) B-474 (I) (O.3.3) B-475 (I) (O.3.4) B-476 (I) (O.3.5) B-477(I) (O.3.6) B-478 (I) (O.3.7) B-479 (I) (O.3.8) B-480 (I) (O.3.9) B-481(I) (O.3.10) B-482 (I) (O.3.11) B-483 (I) (O.3.12) B-484 (I) (O.3.13)B-485 (I) (O.3.14) B-486 (I) (O.3.15) B-487 (I) (O.3.16) B-488 (I)(O.3.17) B-489 (I) (O.3.18) B-490 (I) (O.3.19) B-491 (I) (O.3.20) B-492(I) (O.3.21) B-493 (I) (O.3.22) B-494 (I) (O.3.23) B-495 (I) (O.3.24)B-496 (I) (O.3.25) B-497 (I) (O.3.26) B-498 (I) (O.3.27) B-499 (I)(O.4.1) B-500 (I) (O.4.2) B-501 (I) (O.4.3) B-502 (I) (O.4.4) B-503 (I)(O.4.5) B-504 (I) (O.4.6) B-505 (I) (O.4.7) B-506 (I) (O.4.8) B-507 (I)(O.4.9) B-508 (I) (O.4.10) B-509 (I) (O.4.11) B-510 (I) (O.4.12) B-511(I) (O.4.13) B-512 (I) (O.4.14) B-513 (I) (O.4.15) B-514 (I) (O.4.16)B-515 (I) (O.4.17) B-516 (I) (O.4.18) B-517 (I) (O.4.19) B-518 (I)(O.4.20) B-519 (I) (O.4.21) B-520 (I) (O.4.22) B-521 (I) (O.4.23) B-522(I) (O.4.24) B-523 (I) (O.5.1) B-524 (I) (O.5.2) B-525 (I) (O.5.3) B-526(I) (O.5.4) B-527 (I) (O.5.5) B-528 (I) (O.5.6) B-529 (I) (O.5.7) B-530(I) (O.5.8) B-531 (I) (O.5.9) B-532 (I) (O.6.1) B-533 (I) (O.6.2) B-534(I) (O.6.3) B-535 (I) (O.6.4) B-536 (I) (O.6.5) B-537 (I) (O.6.6) B-538(I) (O.6.7) B-539 (I) (O.7.1) B-540 (I) (O.7.2) B-541 (I) (O.7.3) B-542(I) (O.7.4) B-543 (I) (O.7.5) B-544 (I) (O.7.6) B-545 (I) (O.8.1) B-546(I) (O.8.2) B-547 (I) (O.8.3) B-548 (I) (O.8.4) B-549 (I) (O.8.5) B-550(I) (O.9.1) B-551 (I) (O.9.2) B-552 (I) (O.9.3) B-553 (I) (O.10.1) B-554(I) (O.11.1) B-555 (I) (O.11.2) B-556 (I) (O.11.3) B-557 (I) (O.11.4)B-558 (I) (O.12.1) B-559 (I) (O.13.1) B-560 (I) (O.14.1) B-561 (I)(O.14.2) B-562 (I) (O.15.1) B-563 (I) (O.15.2) B-564 (I) (O.15.3) B-565(I) (O.15.4) B-566 (I) (O.15.5) B-567 (I) (O.15.6) B-568 (I) (O.15.7)B-569 (I) (O.15.8) B-570 (I) (O.15.9) B-571 (I) (O.15.10) B-572 (I)(O.15.11) B-573 (I) (O.16.1) B-574 (I) (O.16.2) B-575 (I) (O.16.3) B-576(I) (O.16.4) B-577 (I) (O.16.5) B-578 (I) (O.16.6) B-579 (I) (O.17.1)B-580 (I) (O.18.1) B-581 (I) (O.18.2) B-582 (I) (O.18.3) B-583 (I)(O.18.4) B-584 (I) (O.18.5) B-585 (I) (O.19.1) B-586 (I) (O.20.1) B-587(I) (O.20.2) B-588 (I) (O.20.3) B-589 (I) (O.21.1) B-590 (I) (O.21.2)B-591 (I) (O.21.3) B-592 (I) (O.21.4) B-593 (I) (O.21.5) B-594 (I)(O.21.6) B-595 (I) (O.21.7) B-596 (I) (O.22.1) B-597 (I) (O.22.2) B-598(I) (O.22.3) B-599 (I) (O.22.4) B-600 (I) (O.23.1) B-601 (I) (O.23.2)B-602 (I) (O.23.3) B-603 (I) (O.24.1) B-604 (I) (O.24.2) B-605 (I)(O.24.3) B-606 (I) (O.24.4) B-607 (I) (O.24.5) B-608 (I) (O.25.1) B-609(I) (O.25.2) B-610 (I) (O.26.1) B-611 (I) (O.26.2) B-612 (I) (O.26.3)B-613 (I) (O.26.4) B-614 (I) (O.26.5) B-615 (I) (O.26.6) B-616 (I)(O.26.7) B-617 (I) (O.26.8) B-618 (I) (O.26.9) B-619 (I) (O.26.10) B-620(I) (O.26.11) B-621 (I) (O.26.12) B-622 (I) (O.26.13) B-623 (I)(O.26.14) B-624 (I) (O.26.15) B-625 (I) (O.26.16) B-626 (I) (O.26.17)B-627 (I) (O.26.18) B-628 (I) (O.27.1) B-629 (I) (O.27.2) B-630 (I)(O.27.3) B-631 (I) (O.27.4) B-632 (I) (O.27.5) B-633 (I) (O.27.6) B-634(I) (O.27.7) B-635 (I) (O.27.8) B-636 (I) (O.27.9) B-637 (I) (O.27.10)B-638 (I) (O.27.11) B-639 (I) (O.27.12) B-640 (I) (O.27.13) B-641 (I)(O.27.14) B-642 (I) (O.27.15) B-643 (I) (O.27.16) B-644 (I) (O.27.17)B-645 (I) (O.27.18) B-646 (I) (O.27.19) B-647 (I) (O.27.20) B-648 (I)(O.27.21) B-649 (I) (O.27.22) B-650 (I) (O.27.23) B-651 (I) (O.27.24)B-652 (I) (O.27.25) B-653 (I) (O.27.26) B-654 (I) (O.27.27) B-655 (I)(O.27.28) B-656 (I) (O.27.29) B-657 (I) (O.27.30) B-658 (I) (O.27.31)B-659 (I) (O.27.32) B-660 (I) (O.27.33) B-661 (I) (O.27.34) B-662 (I)(O.27.35) B-663 (I) (O.27.36) B-664 (I) (O.27.37) B-665 (I) (O.27.38)B-666 (I) (O.27.39) B-667 (I) (O.27.40) B-668 (I) (O.27.41) B-669 (I)(O.27.42) B-670 (I) (O.27.43) B-671 (I) (O.27.44) B-672 (I) (O.27.45)B-673 (I) (O.27.46) B-674 (I) (O.27.47) B-675 (I) (O.27.48) B-676 (I)(O.27.49) B-677 (I) (O.27.50) B-678 (I) (O.27.51) B-679 (I) (O.27.52)B-680 (I) (O.27.53) B-681 (I) (O.27.54) B-682 (I) (O.27.55) B-683 (I)(O.27.56) B-684 (I) (O.27.57) B-685 (I) (O.27.58) B-686 (I) (O.27.59)B-687 (I) (O.27.60) B-688 (I) (O.27.61) B-689 (I) (O.27.62) B-690 (I)(O.27.63) B-691 (I) (O.27.64) B-692 (I) (O.27.65) B-693 (I) (O.27.66)B-694 (I) (O.27.67) B-695 (I) (O.27.68) B-696 (I) (O.27.69) B-697 (I)(O.27.70) B-698 (I) (O.27.71) B-699 (I) (O.27.72) B-700 (I) (O.27.73)B-701 (I) (O.27.74) B-702 (I) (O.27.75) B-703 (I) (O.27.76) B-704 (I)(O.27.77) B-705 (I) (O.27.78) B-706 (I) (O.27.79) B-707 (I) (O.27.80)B-708 (I) (O.27.81) B-709 (I) (O.27.82) B-710 (I) (O.27.83) B-711 (I)(O.27.84) B-712 (I) (O.27.85) B-713 (I) (O.27.86) B-714 (I) (O.27.87)B-715 (I) (O.27.88) B-716 (I) (O.27.89) B-717 (I) (O.27.90) B-718 (I)(O.27.91) B-719 (I) (O.27.92) B-720 (I) (O.27.93) B-721 (I) (O.27.94)B-722 (I) (O.27.95) B-723 (I) (O.27.96) B-724 (I) (O.27.97) B-725 (I)(O.27.98) B-726 (I) (O.27.99) B-727 (I) (O.27.100)

The mixtures of active substances can be prepared as compositionscomprising besides the active ingredients at least one inert ingredient(auxiliary) by usual means, e. g. by the means given for thecompositions of compounds I. Concerning usual ingredients of suchcompositions reference is made to the explanations given for thecompositions containing compounds I. The mixtures of active substancesaccording to the present invention are suitable as fungicides, as arethe compounds of formula I. They are distinguished by an outstandingeffectiveness against a broad spectrum of phytopathogenic fungi,especially from the classes of the Ascomycetes, Basidiomycetes,Deuteromycetes and Peronosporomycetes (syn. Oomycetes). In addition, itis refered to the explanations regarding the fungicidal activity of thecompounds and the compositions containing compounds I, respectively.

I. SYNTHESIS EXAMPLES

The compounds of formula I can be prepared according to the methodsoutlined below.

I.1) Preparation of N′-hydroxy-4-[1-(methylamino)ethyl]benzamidine

To a solution of 4-[1-(methylamino)ethyl]benzonitrile (13 g, 1 eq.) inethanol (150 mL) was added triethylamine (17.4 g, 2.5 eq.) and hydroxylamine (9.5 g, 2 eq.). The mixture was refluxed for 3 hours andconcentrated under reduced pressure. The crude product (13 g) was useddirectly without further purification.

I.2) PreparationN-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanamine

A solution of N′-hydroxy-4-[1-(methylamino)ethyl]benzamidine as obtainedin step 1.1 (35 g, 1.0 eq.) in dichloromethane (400 mL) was treated withtrifluoroacetic anhydride (97 g, 3 eq.) at room temperature. The mixturewas stirred for 1 hour, before it was washed with a saturated aqueoussolutions of sodium bicarbonate and water. The organic layer was driedover sodium sulfate and concentrated under reduced pressure. The crudeproduct (48 g) was that was used directly without further purification.

I.3) PreparationN-methyl-N-[1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]acetamide (Ex-16)

To a solution ofN-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanamine obtained in step 1.2 (8.5 g, 1 eq.) in dichloromethane (100mL) was added triethylamine (5.9 g, 2.2 eq.) and acetyl chloride (2.3 g,1.1 eq.). The mixture was stirred overnight, before it was diluted withdichloromethane and washed with aqueous 1N hydrochloric acid. Theorganic layer was successively washed with a saturated aqueous solutionof sodium chloride, dried over sodium sulfate and freed from solventunder reduced pressure. Flash chromatography on silica gel usingcyclohexane-ethyl acetate provided the titled product (4.95 g).

¹H NMR (CDCl₃): δ [ppm]=1.5 and 1.65 (d, 3H), 2.15 and 2.25 (s, 3H), 2.7(s, 3H), 5.25 and 6.15 (q, 1H), 7.45 (m, 2H), 8.13 (m, 2H).

I.4) Preparation ofN-[[4-[(Z)—N′-hydroxycarbamimidoyl]phenyl]methyl]-N,2-dimethyl-propanamide

To a solution of N-[(4-cyanophenyl)methyl]-N-methyl-acetamide (8.8 g,1.0 eq.) in tetrahydrofuran (50 mL) was added hydroxylaminehydrochloride (4.2 g, 1.5 eq.) and potassium carbonate (4.5 g, 0.8 eq.)in 20 mL water. The mixture was stirred overnight at 23° C. and theprogress of the reaction was monitored by HPLC. It was filtered, washedfive times with toluene and concentrated under reduced pressure toafford the title compound (10 g) that was used directly without furtherpurification.

I.5) Preparation ofN,2-dimethyl-N[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl] phenyl]methyl]propanamide (Ex-13)

A solution ofN-[[4-[(Z)—N′-hydroxycarbamimidoyl]phenyl]methyl]-N,2-dimethyl-propanamideobtained in step I.4 (10 g, 1.0 eq.) in tetrahydrofuran (100 mL) wastreated with trifluoroacetic anhydride (30 g, 3.5 eq.) at roomtemperature. The mixture was stirred for 2 hours, concentrated underreduced pressure and water was added. The aqueous phase was extractedwith ethyl acetate, the combined organic phases were washed with aqueous1N hydrochloric acid and saturated aqueous solution of sodiumbicarbonate. The organic layer was dried over sodium sulfate andconcentrated under reduced pressure. The crude product was dissolved indichloromethane and washed with saturated aqueous solution of sodiumbicarbonate to remove trifluoroacetic acid, and concentrated underreduced pressure to afford the titled product (3 g). Melting point: 55°C.

I.6) Preparation ofN′-hydroxy-4-[(2-oxopyrrolidin-1-yl)methyl]benzamidine

To a solution of 4-[(2-oxopyrrolidin-1-yl)methyl]benzonitrile (0.55 g,1.0 eq.) in ethanol (5 mL) was added hydroxylamine hydrochloride (0.382g, 2 eq.) and triethylamine (0.694 g, 2.5 eq.). The mixture was refluxedfor 4 hours and concentrated under reduced pressure to afford the titlecompound that was used directly without further purification.

I.7) Preparation of1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (Ex-30)

A solution of N′-hydroxy-4-[(2-oxopyrrolidin-1-yl)methyl]benzamidineobtained in step 1.5 (1 g, 1.0 eq.) in dichloromethan (5 mL) was treatedwith trifluoroacetic anhydride (4.5 g, 5 eq.) at room temperature. Themixture was stirred for 2 hours at 23° C., washed with saturated aqueoussolution of sodium bicarbonate and water. The organic layer was driedover sodium sulfate and concentrated under reduced pressure. Flashchromatography on silica gel using cyclohexane-ethyl acetate providedthe titled product (80 mg). ¹H NMR (CDCl₃): δ [ppm]=2.1 (m, 2H), 2.45(m, 2H), 3.3 (m, 3H), 4.5 (s, 2H), 7.4 (m, 2H), 8.13 (m, 2H).

The compounds Ex-1 to Ex-34 listed in Table I were prepared in ananalogous manner.

TABLE I Compounds Ex-1 to Ex-34 of formula I.Ex, wherein A correspondsto subformula (A.4), wherein A is unsubstituted, and wherein the meaningof R¹, R², R³ and R⁴ are as defined in each line, and wherein # denotesthe point of attachment of the NR¹R² group to the CR³R⁴ moiety. I.Ex

HPLC R_(t)*/ (M + H); Ex. or Melting no R³ R⁴ R¹ R² point (° C.) Ex-1CF₃ H CH₃ H 0.94/326 Ex-2 CF₃ H cyclopropyl H 1.28/352 Ex-3 H H CH₃C(═O)—CH₃ 1.09/300 Ex-4 H H allyl C(═O)—CH₃ 1.17/326 Ex-5 H H allylC(═O)—CH₂CH₃ 1.24/340 Ex-6 H H allyl C(═O)—C(CH₃)₃ 1.34/368 Ex-7 H H CH₃C(═O)—CH₂CH₃ 1.16/314 Ex-8 H H CH₃ C(═O)—C(CH₃)₃ 1.29/342 Ex-9 H HCH(CH₃)₂ C(═O)—CH₂CH₃ 1.26/342 Ex-10 H H CH(CH₃)₂ C(═O)—C(CH₃)₃ 1.38/370Ex-11 H H CH₃ C(═O)—CH(CH₂CH₃)₂ 1.26/356 Ex-12 H H CH₃ C(═O)—CH₂CH₂CH₃1.174/328 Ex-13 H H CH₃ C(═O)—CH(CH₃)₂ 1.170/328 Ex-14 H H CH₃C(═O)—CHCH₃CH₂CH₃ 1.21/342 Ex-15 H H H C(═O)—CH₃ 132° C. Ex-16 CH₃ H CH₃C(═O)—CH₃ 1.11/314 Ex-17 CH₃ H CH₃ C(═O)—C(CH₃)₃ 1.36/356 Ex-18 CH₃ HCH₃ C(═O)—CH₂CH₃ 1.20/327 Ex-19 CH₃ H CH₃ C(═O)—CH₂CH₂CH₃ 1.24/341 Ex-20CH₃ H CH₃ C(═O)—CH(CH₂CH₃)₂ 1.36/369 Ex-21 CH₃ H CH₃ C(═O)—CH(CH₃)₂1.24/341 Ex-22 CH₃ H CH₃ C(═O)—CHCH₃CH₂CH₃ 1.30/355 Ex-23 CF₃ H HC(═O)—CH₃ 191° C. Ex-24 H H CH₂CH₃ C(═O)—CH(CH₃)₂ 1.32/341 Ex-25 H HCH₂CH₃ C(═O)—CH₂CH₂CH₃ 1.24/341 Ex-26 H H CH₂CH₃ C(═O)—CH₂CH₃ 1.31/327Ex-27 H H CH₂CH₃ C(═O)—C(CH₃)₃ 1.32/355 Ex-28 H H CH₂CH₃C(═O)—CHCH₃CH₂CH₃ 1.29/355 Ex-29 H H

1.31/367 Ex-30 H H

1.07/311 Ex-31 H H

1.19/339 Ex-32 H H

91° C. Ex-33 H H

1.22/353 Ex-34 H H

1.11; 325 *HPLC: High Performance Liquid Chromatography; HPLC-columnKinetex XB C18 1,7 μ (50 × 2, 1 mm); eluent: acetonitrile/water + 0.1%trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at 60° C.,flow gradient from 0.8 to 1.0 ml/min in 1.5 min). MS: QuadrupolElectrospray Ionisation, 80 V (positive mode). R_(t): retention time inminutes.

II. BIOLOGICAL EXAMPLES FOR FUNGICIDAL ACTIVITY

The fungicidal action of the compounds of formula I was demonstrated bythe following experiments:

A. Glass House Trials

The spray solutions were prepared in several steps: The stock solutionwere prepared: a mixture of acetone and/or dimethylsulfoxide and thewetting agent/emulsifier Wettol, which is based on ethoxylatedalkylphenoles, in a relation (volume) solvent-emulsifier of 99 to 1 wasadded to 25 mg of the compound to give a total of 5 ml. Water was thenadded to total volume of 100 ml. This stock solution was diluted withthe described solvent-emulsifier-water mixture to the givenconcentration.

II.1) Curative control of soy bean rust on soy beans caused byPhakopsora pachyrhizi Leaves of pot-grown soy bean seedlings wereinoculated with spores of Phakopsora pachyrhizi. To ensure the successof the artificial inoculation, the plants were transferred to a humidchamber with a relative humidity of about 95% and 20 to 24° C. for 24hours. The next day the plants were cultivated for 3 days in agreenhouse chamber at 23 to 27° C. and a relative humidity between 60and 80%. Then the plants were sprayed to run-off with an aqueoussuspension, containing the concentration of active ingredient or theirmixture as described below. The plants were allowed to air-dry. Then thetrial plants were cultivated for 14 days in a greenhouse chamber at 23to 27° C. and a relative humidity between 60 and 80%. The extent offungal attack on the leaves was visually assessed as % diseased leafarea.

In this test, the plants which had been treated with 32 ppm of theactive compound Ex-1, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-10, Ex-11,Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-18, Ex-19, Ex-21, Ex-22, Ex-23,Ex-28, Ex-30, Ex-31, Ex-32 and Ex-33 showed a diseased leaf area of atmost 5%, whereas the untreated plants showed 90% diseased leaf area.

II.2) Protective control of soy bean rust on soy beans caused byPhakopsora pachyrhizi Leaves of pot-grown soy bean seedlings weresprayed to run-off with an aqueous suspension, containing theconcentration of active ingredient or their mixture as described below.The plants were allowed to air-dry. The trial plants were cultivated for2 day in a greenhouse chamber at 23 to 27° C. and a relative humiditybetween 60 and 80%. Then the plants were inoculated with spores ofPhakopsora pachyrhizi. To ensure the success the artificial inoculation,the plants were transferred to a humid chamber with a relative humidityof about 95% and 20 to 24° C. for 24 h. The trial plants were cultivatedfor fourteen days in a greenhouse chamber at 23 to 27° C. and a relativehumidity between 60 and 80%. The extent of fungal attack on the leaveswas visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 32 ppm of theactive compound Ex-1, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-10, Ex-11,Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-17, Ex-18, Ex-19, Ex-20, Ex-21,Ex-22, Ex-23, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32 and Ex-33 showed adiseased leaf area of 0%, whereas the untreated plants showed 90%diseased leaf area.

In this test, the plants which had been treated with 16 ppm of theactive compound Ex-24, Ex-25, Ex-26 and Ex-27 showed a diseased leafarea of 0%, whereas the untreated plants showed 90% diseased leaf area.

II.3) Curative control of brown rust on wheat caused by Pucciniarecondite

The first two developed leaves of pot-grown wheat seedling were dustedwith spores of Puccinia recondite. To ensure the success the artificialinoculation, the plants were transferred to a humid chamber withoutlight and a relative humidity of 95 to 99% and 20 to 24° C. for 24hours. The next day the plants were cultivated for 3 days in agreenhouse chamber at 20 to 24° C. and a relative humidity between 65and 70%. Then the plants were sprayed to run-off with an aqueoussuspension, containing the concentration of active ingredient or theirmixture as described below. The plants were allowed to air-dry. Then thetrial plants were cultivated for 8 days in a greenhouse chamber at 20 to24° C. and a relative humidity between 65 and 70%. The extent of fungalattack on the leaves was visually assessed as % diseased leaf area. Inthis test, the plants which had been treated with 63 ppm of the activecompound Ex-1, Ex-4, Ex-5, Ex-7, Ex-8, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13,Ex-14, Ex-15, Ex-16, Ex-18, Ex-19, Ex-21, Ex-23, Ex-31 and Ex-33 showeda diseased leaf area of at most 2%, whereas the untreated plants showed90% diseased leaf area.

II.4) Preventative control of brown rust on wheat caused by Pucciniarecondite

The first two developed leaves of pot-grown wheat seedling were sprayedto run-off with an aqueous suspension, containing the concentration ofactive ingredient or their mixture as described below. Seven days laterthe plants were inoculated with spores of Puccinia recondite. To ensurethe success the artificial inoculation, the plants were transferred to ahumid chamber without light and a relative humidity of 95 to 99% and 20to 24° C. for 24 h. Then the trial plants were cultivated for 6 days ina greenhouse chamber at 20 to 24° C. and a relative humidity between 65and 70%. The extent of fungal attack on the leaves was visually assessedas % diseased leaf area.

In this test, the plants which had been treated with 63 ppm of theactive compound Ex-4, Ex-5, Ex-8, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13 andEx-14 showed a diseased leaf area of at most 12%, whereas the untreatedplants showed 90% diseased leaf area.

The invention claimed is:
 1. A method for combating phytopathogenicharmful fungi, which process comprises treating the fungi or materials,plants, soil or seeds to be protected against fungal attack, with anagrochemically effective amount of at least one compound of formula I

or an N-oxide, or an agriculturally acceptable salt thereof; wherein: Ais group (A.4), which is unsubstituted

and wherein #1 shall denote the position which is bound to thetrifluoromethyloxadiazole moiety and #2 denotes the position, which isconnected to the —C(R³R⁴)—NR¹R² group; R¹, R² independently of eachother are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C(═O)—(C₁-C₆-alkyl),C(═O)—(C₁-C₆-alkoxy), phenyl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl,phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturatedor aromatic mono- or bicyclic heterocycle, wherein the ring member atomsof said mono- or bicyclic heterocycle include besides carbon atomsfurther 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring memberatoms and wherein 1 or 2 carbon ring member atoms of the heterocycle maybe replaced by 1 or 2 groups independently selected from C(═O) andC(═S); and wherein the heteroaryl group in heteroaryl-C₁-C₄-alkyl is a5- or 6-membered aromatic heterocycle, wherein the ring member atoms ofthe heterocyclic ring include besides carbon atoms 1, 2, 3 or 4heteroatoms selected from N, O and S as ring member atoms; and whereinany of the above-mentioned aliphatic or cyclic groups are unsubstitutedor substituted by 1, 2, 3 or up to the maximum possible number ofidentical or different groups R^(1a); or R¹ and R² together with thenitrogen atom to which they are bound form a saturated or partiallyunsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein theheterocycle includes beside one nitrogen atom and one or more carbonatoms no further heteroatom or 1, 2 or 3 further heteroatomsindependently selected from N, O and S as ring member atoms; and whereinone or two CH₂ groups of the heterocycle may be replaced by one or twogroups independently selected from the group of C(═O) and C(═S); andwherein the heterocycle is unsubstituted or substituted by 1, 2, 3, 4 orup to the maximum possible number of identical or different groupsR^(1a); wherein R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₃-C₈-cyclo alkyl, NHSO₂—C₁-C₄-alkyl,(C═O)—(C₁-C₄-alkyl), C(═O)—(C₁-C₄-alkoxy) or C₁-C₆-alkylsulfonyl; R³ isH, CH₃, or CF₃; and, R⁴ is CH₃ or CF₃.
 2. The method of claim 1, whereinR¹ and R² independently of each other are hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, C(═O)—(C₁-C₆-alkyl),C(═O)—(C₁-C₆-alkoxy), phenyl-C₁-C₄-alkyl or phenyl; and wherein any ofthe aliphatic or cyclic groups are unsubstituted or substituted by 1, 2,3 or up to the maximum possible number of identical or different groupsR^(1a) as defined in claim
 1. 3. The method of claim 1, wherein R³ is H.4. The method of claim 1, wherein R¹ is hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,C(═O)—(C₁-C₆-alkyl), C(═O)—(C₁-C₆-alkoxy), phenyl-C₁-C₄-alkyl,heteroaryl-C₁-C₄-alkyl, phenyl, naphthyl or a 3- to 10-memberedsaturated, partially unsaturated or aromatic mono- or bicyclicheterocycle, wherein the ring member atoms of said mono- or bicyclicheterocycle include besides carbon atoms further 1, 2, 3 or 4heteroatoms selected from N, O and S as ring member atoms and wherein 1or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or2 groups independently selected from C(═O) and C(═S); and wherein theheteroaryl group in heteroaryl-C₁-C₄-alkyl is a 5- or 6-memberedaromatic heterocycle, wherein the ring member atoms of the heterocyclicring include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected fromN, O and S as ring member atoms; and wherein any of the above-mentionedaliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3or up to the maximum possible number of identical or different groupsR^(1a) as defined in claim 1; and R² is C(═O)—(C₁-C₆-alkyl) orC(═O)—(C₁-C₆-alkoxy).
 5. The method of claim 1, wherein R¹ and R²together with the nitrogen atom to which they are bound form a saturatedor partially unsaturated mono- or bicyclic 3- to 7-membered heterocycle,wherein the heterocycle includes beside one nitrogen atom and one ormore carbon atoms no further heteroatom or 1, 2 or 3 further heteroatomsindependently selected from N, O and S as ring member atoms; and whereinone or two CH₂ groups of the heterocycle may be replaced by one or twogroups independently selected from the group of C(═O) and C(═S); andwherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up tothe maximum possible number of identical or different groups R^(1a);wherein R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, NHSO₂—C₁-C₄-alkyl,(C═O)—(C₁-C₄-alkyl), C(═O)—(C₁-C₄-alkoxy) or C₁-C₆-alkylsulfonyl.
 6. Themethod of claim 1, wherein R¹ and R² independently of each other arehydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C(═O)—(C₁-C₆-alkyl), C(═O)—(C₁-C₆-alkoxy), phenyl-C₁-C₄-alkyl or phenyl;and wherein any of the aliphatic or cyclic groups are unsubstituted orsubstituted by 1, 2, 3, 4 or up to the maximum possible number ofidentical or different groups R^(1a) as defined in claim
 1. 7. Anagrochemical mixture comprising at least one compound of the formula I

or an N-oxide, or an agriculturally acceptable salt thereof; wherein: Ais group (A.4), which is unsubstituted

and wherein #1 shall denote the position which is bound to thetrifluoromethyloxadiazole moiety and #2 denotes the position, which isconnected to the —C(R³R⁴)—NR¹R² group; R¹, R² independently of eachother are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C(═O)—(C₁-C₆-alkyl),C(═O)—(C₁-C₆-alkoxy), phenyl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl,phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturatedor aromatic mono- or bicyclic heterocycle, wherein the ring member atomsof said mono- or bicyclic heterocycle include besides carbon atomsfurther 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring memberatoms and wherein 1 or 2 carbon ring member atoms of the heterocycle maybe replaced by 1 or 2 groups independently selected from C(═O) andC(═S); and wherein the heteroaryl group in heteroaryl-C₁-C₄-alkyl is a5- or 6-membered aromatic heterocycle, wherein the ring member atoms ofthe heterocyclic ring include besides carbon atoms 1, 2, 3 or 4heteroatoms selected from N, O and S as ring member atoms; and whereinany of the above-mentioned aliphatic or cyclic groups are unsubstitutedor substituted by 1, 2, 3 or up to the maximum possible number ofidentical or different groups R^(1a); or R¹ and R² together with thenitrogen atom to which they are bound form a saturated or partiallyunsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein theheterocycle includes beside one nitrogen atom and one or more carbonatoms no further heteroatom or 1, 2 or 3 further heteroatomsindependently selected from N, O and S as ring member atoms; and whereinone or two CH₂ groups of the heterocycle may be replaced by one or twogroups independently selected from the group of C(═O) and C(═S); andwherein the heterocycle is unsubstituted or substituted by 1, 2, 3, 4 orup to the maximum possible number of identical or different groupsR^(1a); wherein R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, NHSO₂—C₁-C₄-alkyl,(C═O)—(C₁-C₄-alkyl), C(═O)—(C₁-C₄-alkoxy) or C₁-C₆-alkylsulfonyl; R³ isH,—CH₃, or CF₃; and, R⁴ is CH₃ or CF₃; and at least one furtherpesticidally active substance selected from the group consisting ofherbicides, safeners, fungicides, insecticides, and plant growthregulators.
 8. An agrochemical composition, which comprises an auxiliaryand at least one compound of the formula I,

or an N-oxide, or an agriculturally acceptable salt thereof; wherein: Ais group (A.4), which is unsubstituted

and wherein #1 shall denote the position which is bound to thetrifluoromethyloxadiazole moiety and #2 denotes the position, which isconnected to the —C(R³R⁴)—NR¹R² group; R¹, R² independently of eachother are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C(═O)—(C₁-C₆-alkyl),C(═O)—(C₁-C₆-alkoxy), phenyl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl,phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturatedor aromatic mono- or bicyclic heterocycle, wherein the ring member atomsof said mono- or bicyclic heterocycle include besides carbon atomsfurther 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring memberatoms and wherein 1 or 2 carbon ring member atoms of the heterocycle maybe replaced by 1 or 2 groups independently selected from C(═O) andC(═S); and wherein the heteroaryl group in heteroaryl-C₁-C₄-alkyl is a5- or 6-membered aromatic heterocycle, wherein the ring member atoms ofthe heterocyclic ring include besides carbon atoms 1, 2, 3 or 4heteroatoms selected from N, O and S as ring member atoms; and whereinany of the above-mentioned aliphatic or cyclic groups are unsubstitutedor substituted by 1, 2, 3 or up to the maximum possible number ofidentical or different groups R^(1a); or R¹ and R² together with thenitrogen atom to which they are bound form a saturated or partiallyunsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein theheterocycle includes beside one nitrogen atom and one or more carbonatoms no further heteroatom or 1, 2 or 3 further heteroatomsindependently selected from N, O and S as ring member atoms; and whereinone or two CH₂ groups of the heterocycle may be replaced by one or twogroups independently selected from the group of C(═O) and C(═S); andwherein the heterocycle is unsubstituted or substituted by 1, 2, 3, 4 orup to the maximum possible number of identical or different groupsR^(1a); wherein R^(1a) is halogen, cyano, NO₂, OH, SH, NH₂, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, NHSO₂—C₁-C₄-alkyl,(C═O)—(C₁-C₄-alkyl), C(═O)—(C₁-C₄-alkoxy) or C₁-C₆-alkylsulfonyl; R³ isH, CH₃, or CF₃; and R⁴ is CH₃ or CF₃.
 9. The agrochemical compositionaccording to claim 8, wherein the auxiliary is selected from the groupconsisting of anionic, cationic and non-ionic surfactants.
 10. Seedtreated with the agrochemical composition of claim 8 in an amount of thecompound of the formula I, or an N-oxide, or an agriculturallyacceptable salt thereof, of from 0.1 g to 10 kg per 100 kg of seed.